Crossref
journal-article
Elsevier BV
Tetrahedron (78)
References
82
Referenced
56
- Preliminary results of this work were, in part, orally discussed (Tan, Z.; Negishi, E., 215th ACS National Meeting, Dallas, TX, March 29–April 2, 1998, ORGN 0083).
- For reviews, see (a) House, H. O. Modern Synthetic Reactions, 2nd ed.; Benjamin: Menlo Park, CA, 1972; Chapter 9.
-
(b) Jung, M. E. Tetrahedron 1976, 32, 3.
(
10.1016/0040-4020(76)80016-6
) -
(a) Rossi, R. A.; Bunnett, J. F. J. Am. Chem. Soc. 1972, 94, 683.
(
10.1021/ja00757a088
) -
(b) Rossi, R. A.; Bunnett, J. F. J. Org. Chem. 1973, 38, 3020.
(
10.1021/jo00957a021
) -
(c) Bunnett, J. F.; Gloor, B. F. J. Org. Chem. 1973, 38, 4156.
(
10.1021/jo00963a012
) -
(d) Bunnett, J. F.; Gloor, B. F. J. Org. Chem. 1974, 39, 382.
(
10.1021/jo00917a023
) -
(a) Semmelhack, M. F.; Stauffer, R. D.; Rogerson, T. D. Tetrahedron Lett. 1973, 4519.
(
10.1016/S0040-4039(01)87265-8
) -
(b) Millard, A. A.; Rathke, M. W. J. Am. Chem. Soc. 1977, 99, 4833.
(
10.1021/ja00456a055
) - (c) Fauvarque, J. F.; Jutand, A. J. Organomet. Chem. 1979, 177, 273; ibid, 1981, 209, 109.
-
(d) Kuwajima, I.; Urabe, H. J. Am. Chem. Soc. 1982, 104, 6831.
(
10.1021/ja00388a083
) - (e) Kosugi, M.; Hagiwara, I.; Migita, T. Chem. Lett. 1982, 939; ibid, 1983, 839.
-
(f) Kosugi, M.; Hagiwara, I.; Sumiya, T.; Migita, T. Bull. Chem. Soc. Jpn 1984, 57, 242.
(
10.1246/bcsj.57.242
) -
(a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108.
(
10.1021/ja972593s
) -
(b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382.
(
10.1021/ja9727880
) -
(c) Åhman, J.; Wolfe, J. P.; Troutman, M. V.; Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 1918.
(
10.1021/ja973794z
) -
(d) Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473.
(
10.1021/ja983378u
) -
(a) Maloney, M. G.; Pinhey, J. T. J. Chem. Soc., Chem. Commun. 1984, 965.
(
10.1039/C39840000965
) -
(b) Hashimoto, S.; Shinoda, T.; Ikegami, S. J. Chem. Soc., Chem. Commun. 1988, 1137.
(
10.1039/c39880001137
) -
(c) Hashimoto, S.; Miyazaki, Y.; Ikegami, S. Synlett 1996, 324.
(
10.1055/s-1996-5429
) -
(a) Chang, T. C. T.; Rosenblum, M.; Samuels, S. B. J. Am. Chem. Soc. 1980, 102, 5931.
(
10.1021/ja00538a050
) -
(b) Hudrlik, P. F.; Kulkarni, A. K. J. Am. Chem. Soc. 1981, 103, 6251.
(
10.1021/ja00410a060
) -
(c) Wender, P. A.; Holt, D. A.; Sieburth, S. M. J. Am. Chem. Soc. 1983, 105, 3348.
(
10.1021/ja00348a072
) -
(a) Stork, G.; Rosen, P.; Goldman, N. L. J. Am. Chem. Soc. 1961, 83, 2965.
(
10.1021/ja01474a051
) -
(b) Näf, F.; Decorzant, R.; Thommen, W. Helv. Chim. Acta 1975, 58, 1808.
(
10.1002/hlca.19750580635
) -
(c) Fortunato, J. M.; Ganem, B. J. Org. Chem. 1976, 41, 2194.
(
10.1021/jo00874a028
) 10.1246/cl.1987.1007
/ Chem. Lett. by Negishi (1987)-
(a) Guaciaro, M. A.; Wovkulich, P. M.; Smith, III, A. B. Tetrahedron Lett. 1978, 4661.
(
10.1016/S0040-4039(01)85698-7
) - (b) Smith, III, A. B.; Branca, S. J.; Guaciaro, M. A.; Wovkulich, P. M.; Korn, A. Org. Synth. 1983, 61, 57.
- For reviews of Pd- or Ni-catalyzed cross coupling reactions of organozincs and related organometals, see (a) Negishi, E. Acc. Chem. Res. 1982, 15, 340. (b) Negishi, E. In Current Trends in Organic Synthesis; Nozaki, H., Ed.; Pergamon: Oxford, 1983; pp 269. (c) Negishi, E.; Takahashi, T.; Akiyoshi, K. In Catalysis in Organic Reactions; Rylander, P. N., Greenfield, H., Augustine, R. L., Eds.; Mercel Dekker: New York, 1988; pp 381. (d) Negishi, E.; Liu, F. In Cross Coupling Reactions; Diederich, F., Stang, P. J., Eds.; VCH: Weinheim, 1997; p 1. (e) Negishi, E. In Organozinc Reagents: A Practical Approach; Knochel, P., Jones, P., Eds.; Oxford University: Oxford, 1999; pp 213.
-
For example, see (a) Semmelhack, M. F.; Chong, B. P.; Stauffer, R. D.; Rogerson, T. D.; Chong, A.; Jones, L. D. J. Am. Chem. Soc. 1975, 97, 2507.
(
10.1021/ja00842a031
) -
(b) Semmelhack, M. F.; Stauffer, R. D.; Yamashita, A. J. Org. Chem. 1977, 42, 3180.
(
10.1021/jo00439a015
) - For example, see (a) Posner, G. H. Org. React. 1972, 19, 1.
- (b) Lipshutz, B. H. In Organometallics in Synthesis, Schlosser, M., Ed.; Wiley: Chichester, 1994; Chapter 4, pp 283.
10.1016/0040-4039(91)80010-4
/ Tetrahedron Lett. by Negishi (1991)-
(a) Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W.; Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron Lett. 1992, 33, 917.
(
10.1016/S0040-4039(00)91575-2
) -
(b) Alimardanov, A.; Negishi, E. Tetrahedron Lett. 1999, 40, 3839 and pertinent references therein.
(
10.1016/S0040-4039(99)00635-8
) -
(a) Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W. Tetrahedron Lett. 1992, 33, 919.
(
10.1016/S0040-4039(00)91576-4
) -
(b) Pimm, A.; Kocienski, P.; Street, S. D. A. Synlett 1992, 886.
(
10.1055/s-1992-21528
) -
(c) Johnson, C. R.; Braun, M. P. J. Am. Chem. Soc. 1993, 115, 11014.
(
10.1021/ja00076a079
) -
(d) Newhouse, B. J.; Meyers, A. I.; Sirisoma, N. S.; Braun, M. P.; Johnson, C. R. Synlett 1993, 573.
(
10.1055/s-1993-22533
) -
(e) Comins, D. L.; Joseph, S. P.; Chen, X. Tetrahedron Lett. 1995, 36, 9141.
(
10.1016/0040-4039(95)01958-K
) -
(f) Miller, M. W.; Johnson, C. R. J. Org. Chem. 1997, 62, 1582.
(
10.1021/jo962295y
) -
(g) Bosse, F.; Tunoori, A. R.; Maier, M. E. Tetrahedron 1997, 53, 9159.
(
10.1016/S0040-4020(97)00616-9
) -
(h) Kamikubo, T.; Ogasawara, K. Heterocycles 1998, 47, 69.
(
10.3987/COM-97-S(N)5
) - Certain heteroaryl iodides that may be viewed as α-iodoenones, most notably iodouracils, are known to readily undergo Pd-catalyzed cross coupling without their decomposition or other unwanted side reactions presumably due to their aromaticity. These reactions must be strictly distinguished from those nonaromatic α-iodoenones that are discussed in this study. For representative references on the use of aromatic α-iodoenones, see (a) Vincent, P.; Beaucourt, J. P.; Pichat, L. Tetrahedron Lett. 1982, 23, 63. (b) Farina, V.; Hauck, S. I. Synlett 1991, 157. (c) Kundu, N. G.; Dasgupta, S. K. J. Chem. Soc., Perkin Trans. 1 1993, 2657. (d) For a review, see Bergstrom, D. E. Nucleosides Nucleotides 1982, 1, 1.
- Nagata, T.; Ando, Y.; Hirota, A. Biosci. Biotechnol. Biochem. 1992, 56, 810. For an early synthesis of harveynone, see Graham, A. E.; Mckerrecher, D.; Davies, D. H.; Taylor, R. J. Tetrahedron Lett. 1996, 37, 7445.
10.1016/00404-0399(50)1033E-
/ Tetrahedron Lett. by Garlashelli (1995)10.1016/S0040-4039(00)91094-3
/ Tetrahedron Lett. by Sonogashira (1975)10.1021/jo00220a043
/ J. Org. Chem. by Nwokogu (1985)-
(a) Pour, M.; Negishi, E. Tetrahedron Lett. 1996, 37, 4679.
(
10.1016/0040-4039(96)00962-8
) -
(b) Pour, M.; Negishi, E. Tetrahedron Lett. 1997, 38, 525.
(
10.1016/S0040-4039(96)02409-4
) -
(c) Negishi, E.; Pour, M.; Cederbaum, F. E.; Kotora, M. Tetrahedron 1998, 54, 7057.
(
10.1016/S0040-4020(98)00347-0
) 10.1039/CC9960001679
/ Chem. Commun. by Kamikubo (1996)10.1016/S0022-328X(98)01057-2
/ J. Organomet. Chem. by Negishi (1999)-
(a) King, A. O.; Okukado, N.; Negishi, E. J. Chem. Soc., Chem. Commun. 1977, 683.
(
10.1039/c39770000683
) -
(b) King, A. O.; Negishi, E.; Villani, Jr., F. J.; Silveira, Jr., A. J. Org. Chem. 1978, 43, 358.
(
10.1021/jo00396a046
) -
(c) Kotora, M.; Negishi, E. Synthesis 1997, 121.
(
10.1055/s-1997-1513
) -
(d) Negishi, E.; Xu, C.; Tan, Z.; Kotora, M. Heterocycles 1997, 46, 209.
(
10.3987/COM-97-S79
) -
(e) Kotora, M.; Xu, C.; Negishi, E. J. Org. Chem. 1997, 62, 8957.
(
10.1021/jo971552b
) -
(a) Farina, V.; Baker, S. R.; Sapino, Jr., C. Tetrahedron Lett. 1988, 29, 6043.
(
10.1016/S0040-4039(00)82260-1
) -
(b) Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
(
10.1021/ja00025a025
) 10.1016/S0040-4020(01)90392-8
/ Tetrahedron by Esser (1994)10.1055/s-1990-21156
/ Synlett by Cooper (1990)10.1016/S0040-4039(01)86482-0
/ Tetrahedron Lett. by Newton (1979)10.1016/S0040-4020(97)10265-4
/ Tetrahedron by Rossi (1998)-
(a) Hayashi, T.; Konishi, M.; Kumada, M. Tetrahedron Lett. 1979, 21, 1871.
(
10.1016/S0040-4039(00)92802-8
) -
(b) Negishi, E.; Valente, L. F.; Kobayashi, M. J. Am. Chem. Soc. 1980, 102, 3298.
(
10.1021/ja00529a091
) -
(c) Kobayashi, M.; Negishi, E J. Org. Chem. 1980, 45, 5223.
(
10.1021/jo01313a048
) 10.1055/s-1994-25522
/ Synthesis by Adam (1994)10.1021/ja00283a029
/ J. Am. Chem. Soc. by Keinan (1986)10.1055/s-1989-27330
/ Synthesis by Geraghty (1989)10.1021/ja00156a006
/ J. Am. Chem. Soc. by Doris (1995)10.1021/jo00387a025
/ J. Org. Chem. by Nakano (1987)10.1021/om00162a016
/ Organometallics by Berk (1990){'key': '10.1016/S0040-4020(00)00864-4_BIB38', 'first-page': '2972', 'author': 'Conia', 'year': '1970', 'journal-title': 'Bull. Soc. Chim. Fr.'}
/ Bull. Soc. Chim. Fr. by Conia (1970)10.1039/p19720000602
/ J. Chem. Soc. Perkin Trans. 1 by Begbie (1972){'key': '10.1016/S0040-4020(00)00864-4_BIB40', 'first-page': '1232', 'volume': '55', 'author': 'Nasipuri', 'year': '1978', 'journal-title': 'J. Indian Chem. Soc.'}
/ J. Indian Chem. Soc. by Nasipuri (1978)- (a) Gaudemar, M. Bull. Soc. Chim. Fr. 1963, 1475.
-
(b) Courtois, G.; Harama, M.; Migniac, L. J. Organomet. Chem. 1980, 198, 1.
(
10.1016/S0022-328X(00)84657-4
) 10.1021/jo00269a006
/ J. Org. Chem. by Morita (1989)10.1016/S0957-4166(97)00423-0
/ Tetrahedron: Asymmetry by Takahashi (1997)
Dates
Type | When |
---|---|
Created | 23 years, 1 month ago (July 25, 2002, 1:34 p.m.) |
Deposited | 5 years, 7 months ago (Jan. 14, 2020, 11:41 a.m.) |
Indexed | 1 month ago (July 30, 2025, 10:35 a.m.) |
Issued | 24 years, 9 months ago (Dec. 1, 2000) |
Published | 24 years, 9 months ago (Dec. 1, 2000) |
Published Print | 24 years, 9 months ago (Dec. 1, 2000) |
@article{Negishi_2000, title={Strictly Regiocontrolled α-Monosubstitution of Cyclic Carbonyl Compounds with Alkynyl and Alkyl Groups via Pd-Catalyzed Coupling of Cyclic α-Iodoenones with Organozincs}, volume={56}, ISSN={0040-4020}, url={http://dx.doi.org/10.1016/s0040-4020(00)00864-4}, DOI={10.1016/s0040-4020(00)00864-4}, number={52}, journal={Tetrahedron}, publisher={Elsevier BV}, author={Negishi, Ei-ichi and Tan, Ze and Liou, Show-Yee and Liao, Baiqiao}, year={2000}, month=dec, pages={10197–10207} }