Recent Advances in Silver‐Catalyzed Nitrene, Carbene, and Silylene‐Transfer Reactions
10.1002/ejoc.200500602
Crossref journal-article
Wiley
European Journal of Organic Chemistry (311)
Abstract

AbstractSilver salts are commonly used as Lewis acids in organic synthesis. Silver complexes can also exhibit strong oxidation power due to their high oxidation potentials. This review features the recent development of nitrene, carbene and silylene‐transfer reactions catalyzed by silver complexes. Interesting activity was observed in several reactions highlighting the unique redox chemistry of silver. A disilver(I) catalyst was shown to mediate efficient aziridination of simple olefins, intramolecular amidation of saturated C–H bonds and imination of sulfoxides with high regio‐ and stereoselectivity. Silver compounds also catalyze intermolecular carbene insertion into carbon–halogen bonds, carbon–hydrogen bonds, and aromatic systems. In addition, simple silver salts were found to mediate silylene‐transfer reactions to different olefins and alkynes efficiently. Future mechanistic study of these reactions and further exploration of the redox chemistry of silver could lead to more exciting discoveries.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

Bibliography

Li, Z., & He, C. (2006). Recent Advances in Silver‐Catalyzed Nitrene, Carbene, and Silylene‐Transfer Reactions. European Journal of Organic Chemistry, 2006(19), 4313–4322. Portico.

Authors 2
  1. Zigang Li (first)
  2. Chuan He (additional)
References 233 Referenced 165
  2. {'key': 'e_1_2_7_2_2', 'first-page': '121', 'author': 'Kajimoto Y.', 'year': '1998', 'journal-title': 'Kagaku Purosesu'} / Kagaku Purosesu by Kajimoto Y. (1998)
  3. {'key': 'e_1_2_7_3_2', 'first-page': '27', 'volume': '77', 'author': 'Wilkinson S.', 'year': '1999', 'journal-title': 'Chem. Eng. News'} / Chem. Eng. News by Wilkinson S. (1999)
  4. 10.1021/ie50585a025
  5. 10.1021/ie50569a027
  6. 10.1021/ie50492a013
  7. For oxidation or dehydrogenation of alcohols see:
  8. 10.1016/j.ces.2004.08.020
  9. {'key': 'e_1_2_7_9_2', 'first-page': '157', 'volume': '46', 'author': 'Keuler J. N.', 'year': '2001', 'journal-title': 'Prepr. Am. Chem. Soc., Div. Pet. Chem.'} / Prepr. Am. Chem. Soc., Div. Pet. Chem. by Keuler J. N. (2001)
  10. 10.1016/S0920-5861(00)00413-2
  11. {'key': 'e_1_2_7_11_2', 'first-page': '277', 'volume': '6', 'author': 'Jovanovic N. N.', 'year': '1987', 'journal-title': 'Heterog. Catal.'} / Heterog. Catal. by Jovanovic N. N. (1987)
  12. 10.1016/0021-9517(87)90126-6
  13. 10.1016/S0926-860X(96)00264-5
  14. {'key': 'e_1_2_7_14_2', 'first-page': '682', 'volume': '52', 'author': 'Kralik M.', 'year': '1998', 'journal-title': 'Chem. Pap.'} / Chem. Pap. by Kralik M. (1998)
  15. 10.1016/0926-860X(96)00023-3
  16. 10.1021/ja00260a013
  17. For recent reviews see:
  18. 10.1023/B:TOCA.0000024349.28158.f3
  19. 10.1016/S0926-3373(02)00118-2
  20. 10.1023/A:1019147630269
  22. 10.1021/cm00023a024
  23. 10.1016/0021-9517(91)90015-V
  24. 10.1021/la00058a027
  25. For the CO caused electron poisoning see:
  26. 10.1016/S0920-5861(99)00038-3
  27. 10.1016/S0378-7753(99)00315-8
  28. For selective examples see;
  29. 10.1021/jo020691c
  30. 10.1246/cl.2002.1084
  31. 10.1246/bcsj.74.1129
  32. 10.1002/(SICI)1521-3773(19991216)38:24<3701::AID-ANIE3701>3.0.CO;2-D
  33. 10.1021/ja9603315
  35. 10.1246/nikkashi.2002.223
  36. 10.1560/6GRQ-YRVV-6KU3-RHGX
  38. 10.1016/0040-4039(91)85090-R
  39. 10.1016/S0040-4020(02)00984-5
  40. {'key': 'e_1_2_7_40_2', 'first-page': '2219', 'author': 'Ozasa N.', 'year': '2003', 'journal-title': 'Synlett'} / Synlett by Ozasa N. (2003)
  41. 10.1055/s-2001-9715
  42. 10.1021/ja982857q
  43. 10.1021/ja970203w
  44. 10.1016/S0040-4039(00)79964-3
  46. 10.1021/ja0298702
  47. 10.1021/ja039103i
  48. 10.1073/pnas.0307785101
  49. 10.1021/ja049741g
  50. For selective examples see;
  51. 10.1055/s-1979-28825
  52. 10.1016/0040-4039(91)80169-7
  53. 10.1039/p19890002415
  54. {'key': 'e_1_2_7_54_2', 'first-page': '1073', 'author': 'Lathbury D. C.', 'year': '1989', 'journal-title': 'J. Chem. Soc., Chem. Commun.'} / J. Chem. Soc., Chem. Commun. by Lathbury D. C. (1989)
  55. 10.1016/S0040-4020(01)85590-3
  56. 10.1039/c39920000335
  58. 10.1021/jo00102a056
  59. 10.1021/jo00003a013
  60. 10.1021/jo00077a048
  62. 10.1002/(SICI)1099-0690(200003)2000:6<1019::AID-EJOC1019>3.0.CO;2-4
  63. 10.1039/a903587g
  64. 10.1021/jo00123a040
  65. 10.1016/S0040-4039(00)73226-6
  66. 10.1016/S0040-4039(00)96884-9
  67. 10.1016/S0040-4039(00)85140-0
  68. 10.1016/S0040-4039(00)95065-2
  69. 10.1016/S0040-4039(00)85140-0
  70. 10.1039/c39870000243
  71. 10.1016/S0040-4039(02)01128-0
  72. 10.1021/jo020020e
  73. 10.1021/ol047696b
  75. 10.1002/ejoc.200400598
  76. 10.1016/j.tetlet.2004.07.019
  77. 10.1246/cl.1996.727
  78. 10.1021/ol050826b
  79. 10.1021/ol051065f
  81. 10.1002/zaac.19120790125
  82. {'key': 'e_1_2_7_82_2', 'first-page': '199', 'volume': '42', 'author': 'Eggert J.', 'year': '1918', 'journal-title': 'Chem. Ztg.'} / Chem. Ztg. by Eggert J. (1918)
  83. 10.1002/cber.19180510151
  85. {'key': 'e_1_2_7_85_2', 'first-page': '1472', 'author': 'Wei C.', 'year': '2004', 'journal-title': 'Synlett'} / Synlett by Wei C. (2004)
  86. 10.1021/ol035781y
  87. 10.1016/j.tetlet.2004.01.044
  88. 10.1002/adsc.200303148
  89. 10.1002/anie.200353400
  91. 10.1021/ol015830b
  92. 10.1016/j.jorganchem.2003.07.003
  93. 10.1002/1099-0690(200112)2001:23<4391::AID-EJOC4391>3.0.CO;2-D
  95. 10.1021/ja025969x
  96. 10.1021/ja036558z
  97. 10.1016/0957-4166(95)00323-H
  98. 10.1002/anie.200461286
  99. 10.1021/ja046149i
  101. 10.1021/ja030033p
  102. 10.1002/1521-3765(20020503)8:9<2088::AID-CHEM2088>3.0.CO;2-L
  103. 10.1002/adsc.200390052
  104. 10.1021/ja048251l
  105. For an early review see: L. A. Paquette< Synthesis1975 6 347–357. For selected recent reports see:
  106. 10.1246/nikkashi.1999.287
  107. 10.1016/S0040-4039(98)02284-9
  108. 10.1021/ja028649m
  109. 10.1021/ol0349662
  111. {'key': 'e_1_2_7_111_2', 'first-page': '185', 'volume': '16', 'author': 'Pickering W. F.', 'year': '1966', 'journal-title': 'Rev. Pure Appl. Chem.'} / Rev. Pure Appl. Chem. by Pickering W. F. (1966)
  112. 10.1039/B408762C
  113. 10.1039/dt9820002185
  114. 10.1021/jo00133a050
  115. 10.1021/jo00411a003
  116. 10.1016/S0010-8545(00)80324-0
  118. 10.1021/jo0261911
  119. 10.1021/ol0170152
  120. 10.1021/ol025513k
  121. 10.1021/ol0201862
  122. 10.1021/om0205952
  123. 10.1021/ol015828k
  124. 10.1021/ol016824i
  125. 10.1021/ol016861
  126. 10.1039/b503750f
  127. 10.1021/ja050304r
  128. 10.1021/ol047513l
  129. For selected reviews see:
  130. 10.2174/1385272053765024
  131. 10.1055/s-2003-41010
  132. 10.1021/cr020043t
  133. 10.1002/1521-3773(20021004)41:19<3586::AID-ANIE3586>3.0.CO;2-7
  134. 10.1055/s-1998-1652
  135. For selected reports for Rh see:
  136. 10.1002/(SICI)1099-1395(199606)9:6<341::AID-POC791>3.0.CO;2-5
  137. 10.1021/ol0270475
  138. 10.1021/jo00024a008
  139. 10.1021/ja00086a007
  140. 10.1021/jo990356x
  141. 10.1021/ja9913481
  142. 10.1021/ja045845f
  143. 10.1021/ol050896i
  144. 10.1021/ja00265a037
  145. 10.1021/ol049691k
  146. 10.1002/1521-3765(20020402)8:7<1563::AID-CHEM1563>3.0.CO;2-V
  147. 10.1039/c39840001161
  148. For reviews see:
  149. 10.1016/S0010-8545(01)00442-8
  150. {'key': 'e_1_2_7_150_2', 'first-page': '447', 'volume': '23', 'author': 'Srochinski D.', 'year': '1997', 'journal-title': 'Russ. J. Coord. Chem.'} / Russ. J. Coord. Chem. by Srochinski D. (1997)
  151. 10.1016/0010-8545(87)85002-6
  152. 10.1021/ja038668b
  153. S. L. Zheng J. P. Zhang W. T. Wong X. M. Chen J. Am. Chem. Soc.2003 125 6882–6883 and references cited therein. (10.1021/ja029097a)
  154. {'volume-title': 'Catalysis by Di‐ and Polynuclear Cluster Complexes', 'year': '1998', 'author': 'Doyle M. P.', 'key': 'e_1_2_7_154_2'} / Catalysis by Di‐ and Polynuclear Cluster Complexes by Doyle M. P. (1998)
  156. 10.1016/S0020-1693(02)01145-3
  157. 10.1023/B:TOCA.0000003075.67883.4a
  158. For Rh see:
  159. 10.1021/ja028253a
  160. 10.1021/ja010968a
  161. 10.1021/ol0481784
  162. 10.1016/j.tetlet.2004.03.107
  163. Z. Li C. He unpublished results.
  165. 10.1016/S0040-4020(98)00827-8
  166. 10.1016/S0040-4039(98)00864-8
  167. 10.1016/S0040-4039(97)10553-6
  168. 10.1016/S0040-4020(01)00612-3
  169. 10.3987/COM-02-9648
  171. 10.1021/ja028139s
  172. 10.1021/ja011033x
  173. 10.1021/ol035776u
  174. 10.1021/ja0446294
  175. 10.1021/ol049232j
  176. 10.1021/jo0358877
  177. 10.1002/1521-3773(20020916)41:18<3465::AID-ANIE3465>3.0.CO;2-D
  178. 10.1021/ja037072l
  179. 10.1002/anie.200454243
  180. 10.1021/ol0519442
  181. For selected reviews see:
  182. 10.1002/ejoc.200400415
  183. 10.1002/1521-3773(20001117)39:22<3964::AID-ANIE3964>3.0.CO;2-C
  184. 10.1039/a801154k
  185. 10.1016/S0040-4020(98)00222-1
  186. 10.1021/cr940066a
  187. 10.1021/cr00075a013
  188. {'key': 'e_1_2_7_188_2', 'first-page': '38', 'volume': '1', 'author': 'Bachmann W. E.', 'year': '1941', 'journal-title': 'Org. React.'} / Org. React. by Bachmann W. E. (1941)
  189. 10.1039/a903521d
  190. 10.1039/B412053A
  191. 10.1002/anie.199602201
  193. 10.1039/a604927c
  194. 10.1021/cr00028a010
  195. 10.1002/ange.19750870203
  196. {'key': 'e_1_2_7_196_2', 'first-page': '2193', 'volume': '14', 'author': 'Wolfgang K.', 'year': '2002', 'journal-title': 'Eur. J. Org. Chem.'} / Eur. J. Org. Chem. by Wolfgang K. (2002)
  197. {'volume-title': 'Modern Catalytic Methods for Organic Synthesis with Diazo Compounds', 'year': '1998', 'author': 'Doyle M. P.', 'key': 'e_1_2_7_197_2'} / Modern Catalytic Methods for Organic Synthesis with Diazo Compounds by Doyle M. P. (1998)
  198. For thermo and light condition see ref. 46 and 48 for sonication see:
  199. 10.1055/s-1998-2075
  200. 10.1021/ol015891
  201. 10.1021/jo010951a
  203. 10.1246/bcsj.40.2618
  204. 10.1246/bcsj.40.2392
  205. 10.1021/ja01167a101
  206. 10.1039/a801953c
  207. 10.1021/ol034747g
  209. 10.1021/ic950901m
  210. 10.1021/ic9712028
  211. 10.1021/ic0002521
  212. 10.1021/ja034801o
  213. 10.1021/om0499198
  214. 10.1021/om034002e
  215. 10.1016/j.tetlet.2005.02.052
  217. 10.1021/ja016798j
  218. 10.1021/ja0291484
  219. 10.1021/om050024k
  220. 10.1021/ar9900562
  222. 10.1021/om00053a005
  223. 10.1002/ange.19881001023
  224. 10.1002/ange.19840960427
  225. 10.1021/ja020566i
  226. 10.1021/ja042893r
  228. 10.1021/ja0306563
  229. 10.1016/S0040-4020(00)01020-6
  230. 10.1021/jo00002a030
  231. 10.1021/ja0301370
  232. 10.1021/ja047498f
  233. 10.1021/om00090a018
Dates
Type When
Created 19 years, 3 months ago (May 10, 2006, 1:04 p.m.)
Deposited 2 years ago (Sept. 2, 2023, 4:51 a.m.)
Indexed 2 weeks, 1 day ago (Aug. 23, 2025, 1:02 a.m.)
Issued 19 years ago (Sept. 7, 2006)
Published 19 years ago (Sept. 7, 2006)
Published Online 19 years ago (Sept. 7, 2006)
Published Print 18 years, 11 months ago (Oct. 1, 2006)
Funders 0

None

@article{Li_2006, title={Recent Advances in Silver‐Catalyzed Nitrene, Carbene, and Silylene‐Transfer Reactions}, volume={2006}, ISSN={1099-0690}, url={http://dx.doi.org/10.1002/ejoc.200500602}, DOI={10.1002/ejoc.200500602}, number={19}, journal={European Journal of Organic Chemistry}, publisher={Wiley}, author={Li, Zigang and He, Chuan}, year={2006}, month=sep, pages={4313–4322} }