The Mechanisms of the Stille Reaction
10.1002/anie.200300638
Crossref journal-article
Wiley
Angewandte Chemie International Edition (311)
Abstract

AbstractEighteen years ago in Angewandte Chemie John K. Stille reviewed a novel methodology, which eventually became known by his name, for the coupling of organostannanes with organic electrophiles. Since then that seed has blossomed into a multifaceted methodology full of hidden possibilities to explore, discover, and enjoy. Very recent modifications are making synthetic wishes come true that were only dreamed of a few years ago. Moreover, as important advances are being made in the understanding of the mechanistic details of the process, it is becoming increasingly possible to apply this essential reaction and its new variants in a less empirical way. The purpose of this Review is to give a critical account of this progress.

Bibliography

Espinet, P., & Echavarren, A. M. (2004). The Mechanisms of the Stille Reaction. Angewandte Chemie International Edition, 43(36), 4704–4734. Portico.

Authors 2
  1. Pablo Espinet (first)
  2. Antonio M. Echavarren (additional)
References 594 Referenced 887
  1. 10.1002/ange.19860980605
  2. 10.1002/anie.198605081
  3. {'volume-title': 'Comprehensive Organometallic Chemistry II', 'year': '1995', 'author': 'Farina V.', 'key': 'e_1_2_10_2_2'} / Comprehensive Organometallic Chemistry II by Farina V. (1995)
  5. 10.1055/s-1992-26230
  6. {'volume-title': 'Metal‐Catalyzed Cross‐Coupling Reactions', 'year': '1998', 'author': 'Mitchell T. N.', 'key': 'e_1_2_10_5_2'} / Metal‐Catalyzed Cross‐Coupling Reactions by Mitchell T. N. (1998)
  7. 10.1021/cr00039a007
  8. 10.1016/S0022-328X(00)91902-8
  10. 10.1246/cl.1977.301
  11. 10.1246/cl.1977.1423
  12. 10.1016/S0022-328X(02)01270-6
  13. 10.1021/ja00479a077
  14. {'volume-title': 'Organic Reactions', 'year': '1997', 'author': 'Farina V.', 'key': 'e_1_2_10_13_2'} / Organic Reactions by Farina V. (1997)
  15. {'volume-title': 'Palladium Reagents and Catalysts', 'year': '1995', 'author': 'Tsuji J.', 'key': 'e_1_2_10_14_2'} / Palladium Reagents and Catalysts by Tsuji J. (1995)
  17. {'volume-title': 'Classics in Total Synthesis', 'year': '1996', 'author': 'Nicolaou K. C.', 'key': 'e_1_2_10_16_2'} / Classics in Total Synthesis by Nicolaou K. C. (1996)
  18. {'volume-title': 'Classics in Total Synthesis II', 'year': '2003', 'author': 'Nicolaou K. C.', 'key': 'e_1_2_10_17_2'} / Classics in Total Synthesis II by Nicolaou K. C. (2003)
  19. 10.1039/a808261h
  20. 10.1021/ja960040w
  22. 10.1021/ja00063a093
  23. 10.1002/chem.19950010509
  24. 10.1016/S0022-328X(02)01273-1
  25. For reviews see:
  26. 10.1351/pac199466071471
  27. 10.1055/s-1991-20899
  28. {'volume-title': 'Metal‐Catalyzed Cross‐Coupling Reactions', 'year': '1998', 'author': 'Hiyama T.', 'key': 'e_1_2_10_27_2'} / Metal‐Catalyzed Cross‐Coupling Reactions by Hiyama T. (1998)
  29. 10.1007/3-540-45313-X_3
  30. 10.1021/ar020001r
  31. The related coupling of organogermanes has been less explored:
  32. 10.1016/0022-328X(95)05840-L
  33. 10.1021/ol026613t
  34. For reviews see:
  35. 10.1016/S0022-328X(02)01158-0
  36. 10.1002/ange.200201617
  37. 10.1002/anie.200201617
  38. see also reference [21].
  40. 10.1021/ja00767a075
  41. 10.1016/S0022-328X(00)89636-9
  42. {'key': 'e_1_2_10_40_2', 'first-page': '765', 'author': 'Fauvarque J. F.', 'year': '1976', 'journal-title': 'Bull. Soc. Chim. Fr.'} / Bull. Soc. Chim. Fr. by Fauvarque J. F. (1976)
  43. 10.1016/S0022-328X(00)93215-7
  45. 10.1021/ar00083a001
  46. 10.1021/ol030010f
  47. 10.1021/cr020377i
  48. For leading references on palladium‐catalyzed coupling reactions of organoindium compounds see:
  49. 10.1021/ja004195m
  50. 10.1021/ol015975i
  51. 10.1021/ol0345428
  52. 10.1021/ol035883o
  53. For iron‐catalyzed cross‐coupling reactions of alkyl Grignards reactions see:
  54. 10.1002/1521-3757(20020215)114:4<632::AID-ANGE632>3.0.CO;2-M
  55. 10.1002/1521-3773(20020215)41:4<609::AID-ANIE609>3.0.CO;2-M
  56. 10.1021/ja027190t
  58. 10.1002/ange.19941062307
  59. 10.1002/anie.199423791
  60. 10.1021/cr9903048
  61. 10.1039/a827427z
  62. {'volume-title': 'Transition Metal Catalyzed Reactions', 'year': '1999', 'author': 'Reetz M. T.', 'key': 'e_1_2_10_58_2'} / Transition Metal Catalyzed Reactions by Reetz M. T. (1999)
  63. {'volume-title': 'Metal‐Catalyzed Cross‐Coupling Reactions', 'year': '1998', 'author': 'Link J. T.', 'key': 'e_1_2_10_59_2'} / Metal‐Catalyzed Cross‐Coupling Reactions by Link J. T. (1998)
  64. {'volume-title': 'Metal‐Catalyzed Cross‐Coupling Reactions', 'year': '1998', 'author': 'Bräse S.', 'key': 'e_1_2_10_60_2'} / Metal‐Catalyzed Cross‐Coupling Reactions by Bräse S. (1998)
  65. 10.1016/S0040-4039(00)82177-2
  66. 10.1021/cr000024o
  67. 10.1021/ja00025a025
  68. 10.1021/jo00072a028
  70. {'key': 'e_1_2_10_66_2', 'first-page': '1', 'volume': '5', 'author': 'Farina V.', 'year': '1996', 'journal-title': 'Adv. Met.‐Org. Chem.'} / Adv. Met.‐Org. Chem. by Farina V. (1996)
  71. 10.1351/pac199668010073
  73. 10.1021/ja028167a
  74. 10.1021/ol026394b
  76. 10.1021/ja028726d
  77. 10.1021/ja036984k
  78. 10.1002/1521-3757(20020104)114:1<26::AID-ANGE26>3.0.CO;2-O
  79. 10.1002/1521-3773(20020104)41:1<26::AID-ANIE26>3.0.CO;2-9
  80. 10.1021/ja991500z
  81. 10.1021/ja00357a026
  83. 10.1021/ja00080a001
  84. 10.1016/S0040-4039(00)61436-3
  85. 10.1021/ja00177a048
  86. 10.1246/bcsj.54.1857
  87. 10.1246/bcsj.54.1868
  89. 10.1021/ic00090a025
  90. 10.1021/om970721f
  91. 10.1021/ja00535a018
  92. 10.1021/cr000664r
  93. 10.1021/cr000003u
  95. 10.1002/ange.200301681
  96. 10.1002/anie.200301681
  97. 10.1021/ja038328q
  99. 10.1021/ja00163a060
  100. 10.1021/ja00048a011
  101. 10.1021/om00054a018
  102. 10.1063/1.1388040
  103. 10.1021/ja00195a063
  104. 10.1021/ja00534a029
  105. 10.1002/1521-3765(20000915)6:18<3372::AID-CHEM3372>3.0.CO;2-V
  107. {'volume-title': 'The Chemistry of the Metal‐Carbon Bond', 'year': '1985', 'author': 'Stille J. K.', 'key': 'e_1_2_10_101_2'} / The Chemistry of the Metal‐Carbon Bond by Stille J. K. (1985)
  108. 10.1021/ar50120a002
  109. {'volume-title': 'Current Methods in Inorganic Chemistry', 'year': '2003', 'author': 'Komiya S.', 'key': 'e_1_2_10_103_2'} / Current Methods in Inorganic Chemistry by Komiya S. (2003)
  110. 10.1246/cl.1987.751
  112. 10.1016/S0022-328X(00)84336-3
  113. 10.1016/0022-328X(89)85347-1
  114. 10.1023/A:1011338029948
  115. 10.1021/om021022s
  116. 10.1246/cl.1991.615
  117. 10.1016/0022-328X(95)05472-2
  118. 10.1021/om9709502
  119. 10.1021/om961094h
  121. 10.1021/om980633a
  122. 10.1021/om981043f
  123. 10.1002/(SICI)1521-3765(19991001)5:10<3066::AID-CHEM3066>3.0.CO;2-F
  124. 10.1021/om0104971
  125. 10.1021/om020380s
  126. M. A. F. Hernandez‐Gruel P. Espinet unpublished results.
  128. 10.1039/b304960d
  129. 10.1016/j.tetlet.2003.11.014
  130. 10.1016/S0022-328X(00)86726-1
  131. 10.1021/om00004a038
  133. 10.1021/om00029a025
  134. 10.1021/om00029a026
  135. 10.1021/cr9902704
  136. 10.1039/c29700001065
  137. 10.1016/S0022-328X(00)91277-4
  138. 10.1039/c3973000207b
  139. 10.1021/ic50138a020
  140. 10.1016/0022-328X(88)80689-2
  141. 10.1021/ic50130a043
  142. The rates of oxidative addition are probably different depending on whether [Pd2(dba)3⋅dba] or [Pd2(dba)3]⋅(S) is used as the starting complex as an excess of dba can retard the reaction. However the actual solvento complex used in catalytic transformations is probably not very important. Herein we refer to these complexes as [Pd2(dba)3].
  143. 10.1021/om00138a004
  144. For reviews see:
  145. 10.1016/S0010-8545(98)00073-3
  146. 10.1002/ejic.200300069
  147. 10.1021/ja9637098
  148. 10.1016/S0020-1693(97)06015-5
  149. 10.1021/om020364v
  150. 10.1021/om00032a045
  151. 10.1021/om971064u
  152. 10.1002/1521-3765(20010518)7:10<2134::AID-CHEM2134>3.0.CO;2-9
  153. 10.1016/S0022-328X(98)00877-8
  154. 10.1021/om020439v
  155. 10.1021/om9906417
  156. 10.1021/ja028738z
  157. 10.1021/ja9637098
  158. 10.1021/om020838q
  159. 10.1002/1521-3765(20010316)7:6<1273::AID-CHEM1273>3.0.CO;2-7
  160. 10.1021/ar980063a
  161. 10.1021/om00045a012
  162. 10.1021/om00004a039
  163. 10.1021/jo00126a037
  164. 10.1021/om00012a029
  166. 10.1021/om030132b
  167. 10.1002/1099-0682(200211)2002:11<3028::AID-EJIC3028>3.0.CO;2-8
  168. 10.1021/om0101137
  169. 10.1039/C39860001338
  170. 10.1002/(SICI)1521-3757(19980216)110:4<492::AID-ANGE492>3.0.CO;2-7
  171. 10.1002/(SICI)1521-3773(19980302)37:4<481::AID-ANIE481>3.0.CO;2-I
  172. 10.1016/0022-328X(89)87132-3
  173. 10.1021/ja00022a026
  174. 10.1021/ja00074a018
  175. 10.1002/chem.19960020810
  176. 10.1002/1099-0682(200207)2002:7<1711::AID-EJIC1711>3.0.CO;2-X
  177. 10.1021/om00004a038
  178. 10.1021/ja00120a012
  180. 10.1246/cl.1995.367
  181. 10.1246/bcsj.72.573
  182. {'key': 'e_1_2_10_170_2', 'first-page': '925', 'author': 'Yamamoto A.', 'year': '2000', 'journal-title': 'Synlett'} / Synlett by Yamamoto A. (2000)
  183. 10.1021/ja001511o
  184. 10.1039/b008811k
  185. 10.1021/om030298c
  187. 10.1021/ja035835z
  188. 10.1021/om034187p
  189. 10.1002/1521-3757(20021115)114:22<4350::AID-ANGE4350>3.0.CO;2-0
  190. 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO;2-U
  191. 10.1021/ja028966t
  192. For Highlights on the coupling of alkyl electrophiles see:
  193. 10.1002/(SICI)1521-3757(19991018)111:20<3201::AID-ANGE3201>3.0.CO;2-Z
  194. 10.1002/(SICI)1521-3773(19991018)38:20<3018::AID-ANIE3018>3.0.CO;2-F
  195. 10.1002/ange.200390091
  196. 10.1002/anie.200390123
  197. 10.1021/cr00028a008
  199. 10.1021/ja00205a039
  200. 10.1039/c39890001816
  201. 10.1021/om00042a008
  203. 10.1002/(SICI)1521-3757(19980803)110:15<2154::AID-ANGE2154>3.0.CO;2-C
  204. 10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO;2-L
  205. 10.1021/ja037425g
  207. 10.1021/ja9727880
  208. 10.1021/ja981318i
  209. 10.1021/ja9721881
  210. 10.1021/ja983378u
  211. 10.1021/ar0201106
  213. 10.1021/ja972593s
  214. 10.1021/ja973794z
  215. 10.1021/ja037932y
  217. 10.1021/jo990805t
  218. 10.1021/om9900162
  219. 10.1016/S0040-4039(98)02597-0
  221. 10.1016/S0040-4039(99)00642-5
  222. 10.1021/jo990805t
  224. 10.1021/ja00408a068
  225. 10.1246/cl.1983.1725
  226. 10.1021/om00139a009
  227. 10.1002/(SICI)1521-3757(19981217)110:24<3586::AID-ANGE3586>3.0.CO;2-7
  228. 10.1002/(SICI)1521-3773(19981231)37:24<3387::AID-ANIE3387>3.0.CO;2-P
  229. For Heck reactions see:
  230. 10.1021/jo9820059
  231. 10.1021/ja010988c
  232. For the amination of aryl bromides and aryl chlorides with [Pd(PtBu3)2] see:
  233. 10.1016/S0040-4039(97)10659-1
  234. 10.1016/S0040-4039(98)00202-0
  235. 10.1021/jo990408i
  236. 10.1021/jo0258913
  237. For other related phosphanes for the activation of aryl chlorides see:
  238. 10.1021/jo010983y
  239. 10.1021/jo010764c
  240. 10.1002/1521-3757(20010417)113:8<1561::AID-ANGE1561>3.0.CO;2-0
  241. 10.1002/1521-3773(20010417)40:8<1513::AID-ANIE1513>3.0.CO;2-C
  242. 10.1002/1521-3757(20001117)112:22<4315::AID-ANGE4315>3.0.CO;2-L
  243. 10.1002/1521-3773(20001117)39:22<4153::AID-ANIE4153>3.0.CO;2-T
  244. 10.1039/b107888g
  245. 10.1016/S0040-4039(02)02189-5
  247. 10.1021/jo0347056
  248. {'key': 'e_1_2_10_229_2', 'first-page': '2069', 'author': 'Wolf C.', 'year': '2003', 'journal-title': 'Synlett'} / Synlett by Wolf C. (2003)
  249. 10.1021/ol016971g
  251. 10.1021/ja0157402
  252. 10.1021/jo016226h
  254. 10.1021/ja982250
  255. 10.1002/(SICI)1521-3757(19990816)111:16<2570::AID-ANGE2570>3.0.CO;2-S
  256. 10.1002/(SICI)1521-3773(19990816)38:16<2413::AID-ANIE2413>3.0.CO;2-H
  257. 10.1021/jo000674s
  258. 10.1021/ja992130h
  259. 10.1021/ja036947t / J. Am. Chem. Soc. by Nguyen H. N. (2003)
  260. 10.1021/jo025732j
  261. 10.1039/b006791l
  262. For Suzuki coupling reactions with Pd0complexes of 15‐membered macrocyclic trienes see:
  263. 10.1002/(SICI)1099-0690(200001)2000:2<239::AID-EJOC239>3.0.CO;2-R
  264. 10.1016/S0040-4039(02)00028-X
  265. 10.1002/ange.200351189
  266. 10.1002/anie.200351189
  267. 10.1021/ja0344563
  268. 10.1002/ange.200352668
  269. 10.1002/anie.200352668
  270. 10.1002/ange.200352858
  271. 10.1002/anie.200352858
  272. 10.1021/ja0283899
  274. 10.1021/ja038177r
  275. 10.1021/ja0393729
  276. 10.1021/ja0449527
  277. 10.1021/ja020012f
  278. For coupling reactions with fluorostannates see:
  279. 10.1055/s-1994-23081
  280. 10.1021/ol005666c
  281. 10.1021/jo970465g
  282. 10.1055/s-1998-1942
  283. 10.1021/jo00105a036
  284. 10.1021/om00006a053
  285. 10.1021/ja00092a058
  286. 10.1021/ja00124a026
  287. 10.1021/ja037959h
  288. 10.1021/ja0034592
  289. 10.1002/1521-3757(20020517)114:10<1838::AID-ANGE1838>3.0.CO;2-V
  290. 10.1002/1521-3773(20020517)41:10<1760::AID-ANIE1760>3.0.CO;2-3
  291. 10.1021/ja00435a017
  292. 10.1021/ja0361493
  293. 10.1021/ja0264394
  294. 10.1021/ja026885r
  295. 10.1021/jo0265277
  296. 10.1021/ja026975w
  297. For Suzuki coupling reactions in the absence of ligands see:
  298. 10.1021/jo00096a056
  299. 10.1016/S0040-4039(98)00757-6
  300. 10.1016/S0040-4039(97)00171-8
  301. 10.1021/jo970439i
  302. 10.1055/s-1998-22661
  303. 10.1021/ja035044x
  304. Intriguingly the Suzuki reaction of aryl iodides and aryl bromides with some aryl boronic acids has been carried out in the absence of a metal as a catalyst in water at 150 °C (microwave irradiation):
  305. 10.1002/ange.200390334
  306. 10.1002/anie.200390362
  307. 10.1021/jo034230i
  308. 10.1021/ol035485l
  309. 10.1002/ange.200301672
  310. 10.1002/anie.200301672
  311. 10.1021/ol035184b
  313. {'key': 'e_1_2_10_287_2', 'first-page': '1103', 'volume': '274', 'author': 'Bumagin N. A.', 'year': '1984', 'journal-title': 'Dokl. Akad. Nauk SSSR'} / Dokl. Akad. Nauk SSSR by Bumagin N. A. (1984)
  314. 10.1016/0022-328X(83)85077-3
  315. 10.1021/ar020267y
  316. 10.1021/la990144v
  317. 10.1021/ja016315b
  318. For reviews see:
  319. 10.1002/1521-3757(20020415)114:8<1342::AID-ANGE1342>3.0.CO;2-A
  320. 10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO;2-Y
  321. 10.1016/S0065-3055(00)46004-1
  322. 10.1021/cr940472u
  323. 10.1002/ange.19971092006
  324. 10.1002/anie.199721621
  325. 10.1021/jo990554o
  326. 10.1021/ja038631r
  327. 10.1002/1521-3765(20020902)8:17<3901::AID-CHEM3901>3.0.CO;2-E
  328. 10.1021/ol035147k
  330. 10.1016/S0022-328X(98)00455-0
  331. 10.1021/om9809771
  332. 10.1021/om020552l
  333. 10.1016/S0022-328X(03)00476-5
  334. 10.1021/om030099t
  335. Known palladium–NHC complexes are μ2‐bridged dimers:
  336. 10.1021/ol0260831
  337. 10.1002/1521-3757(20020415)114:8<1421::AID-ANGE1421>3.0.CO;2-E
  338. 10.1002/1521-3773(20020415)41:8<1363::AID-ANIE1363>3.0.CO;2-G
  339. 10.1021/ja035565k
  340. 10.1002/1099-0682(200108)2001:8<1917::AID-EJIC1917>3.0.CO;2-M
  341. 10.1039/B211298C
  342. 10.1002/1521-3757(20021004)114:19<3820::AID-ANGE3820>3.0.CO;2-I
  343. 10.1002/1521-3773(20021004)41:19<3668::AID-ANIE3668>3.0.CO;2-U
  344. 10.1021/ol0058644
  345. 10.1021/jo025619t
  346. 10.1002/1615-4169(200202)344:2<172::AID-ADSC172>3.0.CO;2-9
  347. 10.1002/1521-3757(20020104)114:1<187::AID-ANGE187>3.0.CO;2-A
  348. 10.1002/1521-3773(20020104)41:1<179::AID-ANIE179>3.0.CO;2-O
  349. 10.1002/ange.19951071709
  350. 10.1002/anie.199518481
  351. 10.1039/b100328n
  352. 10.1039/a806041j
  353. 10.1039/b008470k
  354. 10.1039/b004793g
  355. 10.1021/ol0063048
  356. {'journal-title': 'Chem. Commun.', 'first-page': '1999', 'author': 'Weissman H.', 'key': 'e_1_2_10_324_2'} / Chem. Commun. by Weissman H.
  357. 10.1016/S0022-328X(00)00876-7
  358. 10.1002/1615-4169(20010226)343:4<338::AID-ADSC338>3.0.CO;2-I
  359. 10.1021/ol027337l
  360. 10.1039/b208545n
  362. 10.1021/ja003191e
  363. 10.1021/ja005872f
  364. 10.1016/S0040-4020(96)01060-5
  365. 10.1039/b300033h
  366. 10.1002/1521-3765(20021104)8:21<4843::AID-CHEM4843>3.0.CO;2-I
  368. 10.1039/cs9851400197 / Ligand substitution reactions of square‐planar molecules by Cross R. (1985)
  369. 10.1016/S0898-8838(08)60018-5
  370. 10.1080/02603599008035817
  371. 10.1021/om00006a055
  372. 10.1016/S0898-8838(03)54002-8
  373. 10.1021/ja00203a016
  374. 10.1021/ic00047a028
  375. 10.1002/ejic.200300756
  376. 10.1021/ja00191a036
  377. 10.1021/ja00191a037
  378. 10.1021/om030524i
  379. 10.1021/ja00151a033
  380. 10.1021/ja9742388
  381. 10.1021/ja0204978
  383. 10.1002/ange.19941062315
  384. 10.1002/anie.199424451
  385. 10.1002/chem.19960021219
  386. 10.1021/om970085l
  387. 10.1021/om0202524
  388. 10.1021/ja980901w
  389. 10.1021/ja00815a009
  391. 10.1021/ja00094a083
  392. 10.1021/jo982210o
  393. 10.1021/ic980101m
  394. 10.1002/1521-3765(20010601)7:11<2481::AID-CHEM24810>3.0.CO;2-2
  395. 10.1021/ja011644p
  396. 10.1021/om00112a010
  397. 10.1021/om00117a025
  398. 10.1039/dt9910001881
  399. 10.1021/om00162a034
  400. 10.1039/dt9920000697
  401. 10.1021/om00060a056
  402. 10.1016/0022-328X(94)05331-5
  403. 10.1016/0022-328X(94)05471-M
  404. 10.1021/om960516k
  405. 10.1021/om971094x
  407. 10.1021/om00007a011
  408. 10.1021/om9601965
  409. 10.1021/om980167p
  410. 10.1021/om020043j
  411. 10.1002/ange.200390003
  412. 10.1002/anie.200390035
  414. 10.1021/ja011306o
  415. 10.1002/1521-3757(20021104)114:21<4218::AID-ANGE4218>3.0.CO;2-8
  416. 10.1002/1521-3773(20021104)41:21<4056::AID-ANIE4056>3.0.CO;2-8
  417. 10.1002/1521-3757(20021018)114:20<4066::AID-ANGE4066>3.0.CO;2-D
  418. 10.1002/1521-3773(20021018)41:20<3910::AID-ANIE3910>3.0.CO;2-W
  419. 10.1021/ja0349352
  420. 10.1021/ja0363258
  421. 10.1021/ja029021e
  422. 10.1021/ja0315107
  423. 10.1016/S0010-8545(99)00210-6
  424. Both the ability of SnIVto increase its coordination number and the formation of single‐bridged compounds are well documented:
  425. {'volume-title': 'Comprehensive Organometallic Chemistry II', 'year': '1995', 'author': 'Davies A. G.', 'key': 'e_1_2_10_389_2'} / Comprehensive Organometallic Chemistry II by Davies A. G. (1995)
  426. {'volume-title': 'Comprehensive Coordination Chemistry', 'year': '1987', 'author': 'Harrison P. G.', 'key': 'e_1_2_10_390_2'} / Comprehensive Coordination Chemistry by Harrison P. G. (1987)
  427. {'volume-title': 'Comprehensive Organometallic Chemistry', 'year': '1982', 'author': 'Davies A. G.', 'key': 'e_1_2_10_391_2'} / Comprehensive Organometallic Chemistry by Davies A. G. (1982)
  428. For R‐bridging structures characterized by X‐ray diffraction see:
  429. 10.1021/ja00095a019
  430. 10.1021/ja00063a036
  431. 10.1039/DT9890000169
  432. 10.1021/om00101a005
  433. 10.1002/ange.19961080610
  434. 10.1002/anie.199606571
  435. 10.1021/ja00271a037
  437. 10.1021/ja00252a029
  438. 10.15227/orgsyn.071.0097
  439. However LiCl retards some intramolecular couplings:
  440. 10.1039/c39850000809
  441. 10.1021/jo00367a042
  442. 10.1016/0040-4039(96)01698-X
  443. 10.1021/om970492x
  445. 10.1016/0040-4039(94)02191-D
  446. 10.1016/0040-4039(95)00485-U
  447. 10.1021/jo971681s
  448. 10.1021/ja012711i
  449. 10.1039/c39920001440
  450. 10.1021/ja00042a044
  451. 10.1021/ol005641d
  452. 10.1021/jo0200318
  453. 10.1002/ange.200250205
  454. 10.1002/anie.200250205
  455. 10.1021/ja0160593
  456. 10.1021/om020519z
  457. 10.1021/cr00089a003
  458. 10.1039/a807799a
  460. 10.1016/0020-1693(94)03876-7
  461. 10.1021/om00051a039
  462. The same effect has been observed in other reductive eliminations:
  463. 10.1021/ja981428p
  464. 10.1021/ja980762i
  465. For earlier studies see:
  466. 10.1016/S0040-4039(01)86864-7
  467. 10.1021/ja00313a032
  468. 10.1002/(SICI)1099-0682(199802)1998:2<155::AID-EJIC155>3.0.CO;2-T
  470. 10.1021/om00121a047
  471. 10.1021/ja00329a079
  472. 10.1021/ja00369a028
  473. 10.1016/S0040-4020(01)91417-6
  474. 10.1016/0022-328X(88)80456-X
  476. 10.1016/S0022-328X(00)93414-4
  477. 10.1039/C39940001099
  478. 10.1016/0022-328X(88)87011-6
  479. 10.1021/ja00255a017
  480. 10.1016/0304-5102(92)80265-I
  481. 10.1016/S0040-4039(00)85170-9
  483. 10.1016/S0040-4039(00)92814-4
  484. 10.1021/jo00174a027
  485. 10.1246/cl.1987.1237
  486. 10.1016/S0040-4039(00)92815-6
  487. 10.1021/om0000966
  488. 10.1002/1099-0690(20021)2002:1<15::AID-EJOC15>3.0.CO;2-0
  489. 10.1021/ja002931g
  490. 10.1002/1521-3765(20001201)6:23<4413::AID-CHEM4413>3.0.CO;2-R
  491. 10.1016/S0022-328X(00)81072-4
  492. 10.1002/(SICI)1521-3757(19990201)111:3<356::AID-ANGE356>3.0.CO;2-I
  493. 10.1002/(SICI)1521-3773(19990201)38:3<343::AID-ANIE343>3.0.CO;2-X
  494. 10.1021/om000765f
  495. 10.1002/ange.19850970407
  496. 10.1002/anie.198502831
  497. 10.1021/om00039a023
  498. 10.1002/1521-3765(20020816)8:16<3620::AID-CHEM3620>3.0.CO;2-P
  499. 10.1021/ja003718n
  500. 10.1021/ja00138a012
  501. 10.1021/ja00016a082
  502. 10.1021/jo00106a006
  503. 10.1021/ja972554g
  504. 10.1021/om0001265
  505. See also:
  506. {'key': 'e_1_2_10_466_2', 'first-page': '345', 'volume': '20', 'author': 'Vicente J.', 'year': '1996', 'journal-title': 'New J. Chem.'} / New J. Chem. by Vicente J. (1996)
  507. 10.1021/om9905963
  508. 10.1021/om980283s
  510. 10.1021/om00141a036
  511. 10.1016/0022-328X(87)80292-9
  512. 10.1021/om00103a023
  514. 10.1021/om0007466
  515. 10.1021/om030035i
  516. 10.1021/ja00511a031
  517. 10.1021/om00017a063
  519. 10.1016/0022-328X(86)80264-9
  520. 10.1021/ja00176a052
  521. 10.1021/jo00103a068
  522. 10.1016/0040-4039(96)01568-7
  523. 10.1016/S0040-4039(97)01026-5
  524. 10.3987/COM-97-7994
  525. 10.1016/S0040-4039(97)10584-6
  526. 10.1016/S0040-4039(98)01058-2
  527. 10.1021/jo991116k
  528. 10.1021/ja037409j
  529. 10.1021/ja037409j
  531. 10.1016/S0040-4039(97)01121-0
  532. 10.1016/S0022-328X(98)01056-0
  533. 10.1021/ja974206k
  534. 10.1021/om000828u
  535. 10.1055/s-1997-997
  536. 10.1016/S0022-328X(02)02153-8
  537. Density functional calculations on the oxidative addition of alkynyl stannanes to [PdL2]:
  538. 10.1021/om020208o
  539. 10.1021/om0303449
  541. 10.1021/ja992597s
  542. 10.1021/ol0000861
  543. 10.1016/j.jorganchem.2003.07.027
  545. 10.1021/ja9639832
  546. 10.1021/om0000966
  548. {'key': 'e_1_2_10_508_2', 'first-page': '636', 'author': 'Bumagin N. A.', 'year': '1984', 'journal-title': 'Izv. Akad. Nauk SSSR Ser. Khim.'} / Izv. Akad. Nauk SSSR Ser. Khim. by Bumagin N. A. (1984)
  549. 10.1021/ol0257777
  551. 10.1021/ar00014a005
  552. 10.1595/003214093X37127 / Platinum Metals Rev. by Canty A. J. (1993)
  553. 10.1021/cr9704671
  554. 10.1021/om980065z
  555. The X‐ray crystal structure of a PdIVcomplex formed by oxidative addition of PhI to a PdIIcomplex was published. This structure included several improbable features:
  556. 10.1039/b005521m
  557. {'key': 'e_1_2_10_517_2', 'first-page': '1869', 'author': 'Brunel J. M.', 'year': '2001', 'journal-title': 'Chem. Commun.'} / Chem. Commun. by Brunel J. M. (2001)
  558. {'key': 'e_1_2_10_517_3', 'first-page': '2298', 'author': 'Brunel J. M.', 'year': '2001', 'journal-title': 'Chem. Commun.'} / Chem. Commun. by Brunel J. M. (2001)
  559. Chem. Commun.2002 May 16).
  560. 10.1002/1521-3765(20010417)7:8<1703::AID-CHEM17030>3.0.CO;2-K
  562. 10.1016/S0022-328X(00)83563-9
  563. 10.1080/00945717708055962
  564. 10.1021/ja025828v
  565. 10.1016/0022-328X(85)87007-8
  567. 10.1021/jo00306a012
  568. 10.1021/jo00054a025
  569. 10.1021/jo00011a011
  570. 10.1021/jo00059a064
  571. 10.1021/jo034788q
  573. 10.1002/ange.200353015
  574. 10.1002/anie.200353015
  575. 10.1021/ol035632f
  576. 10.1021/jo00099a018
  577. 10.1021/om020896b
  578. 10.1002/ange.200352979
  579. 10.1002/anie.200352979
  580. 10.1021/jo00066a006
  581. 10.1246/cl.1995.771
  583. 10.1021/ja00127a010
  584. 10.1021/ol035458v
  585. 10.1021/jo961161h
  586. 10.1021/ja9541239
  587. 10.1021/jo9700078
  588. 10.1021/ol034962x
  589. 10.1021/jo970656j
  590. 10.1021/ol034962x
  591. 10.1021/ol027569k
  592. 10.1021/ol027453o
  593. 10.1021/ol0273497
  594. 10.1021/ja037043a
Dates
Type When
Created 21 years ago (Aug. 27, 2004, 12:06 p.m.)
Deposited 8 months, 2 weeks ago (Dec. 18, 2024, 6:56 a.m.)
Indexed 1 week, 1 day ago (Aug. 28, 2025, 8:10 a.m.)
Issued 20 years, 11 months ago (Sept. 7, 2004)
Published 20 years, 11 months ago (Sept. 7, 2004)
Published Online 20 years, 11 months ago (Sept. 7, 2004)
Published Print 20 years, 11 months ago (Sept. 13, 2004)
Funders 0

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@article{Espinet_2004, title={The Mechanisms of the Stille Reaction}, volume={43}, ISSN={1521-3773}, url={http://dx.doi.org/10.1002/anie.200300638}, DOI={10.1002/anie.200300638}, number={36}, journal={Angewandte Chemie International Edition}, publisher={Wiley}, author={Espinet, Pablo and Echavarren, Antonio M.}, year={2004}, month=sep, pages={4704–4734} }