Palladium-catalyzed carbene insertion into vinyl halides and trapping with amines

被引：106

作者：

Devine, Sean K. J. ^{[1
]}

Van Vranken, David L. ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 10期

关键词：

D O I：

10.1021/ol070758o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium is shown to catalyze the three- component coupling of vinyl halides, trimethylsilyldiazomethane, and amines to generate allylamines. The mechanism is believed to involve formation of an R-Pd=CHSiMe3 intermediate that undergoes migration of the vinyl ligand to the empty p-orbital of the carbene ligand. The resulting eta(1)-allylpalladium species forms an eta(3)-allylpalladium intermediate that is trapped by the amine nucleophile. Under the conditions tested, cyclic secondary amines and terminal vinyl iodides give the best results.

引用

页码：2047 / 2049

页数：3

共 19 条

[11] Use of a bulky phosphine of weak σ-donicity with palladium as a versatile and highly-active catalytic system:: allylation and arylation coupling reactions at 10-1-10-4 mol% catalyst loadings of ferrocenyl bis(difurylphosphine)/Pd
Hierso, JC
Fihri, A
Amardeil, R
Meunier, P
Doucet, H
Santelli, M
[J]. TETRAHEDRON, 2005, 61 (41) : 9759 - 9766
[12] Palladium-mediated polymerization of alkyl diazoacetates to afford poly(alkoxycarbonylmethylene)s. First synthesis of polymethylenes bearing polar substituents
Ihara, E
Haida, N
Iio, M
Inoue, K
[J]. MACROMOLECULES, 2003, 36 (01) : 36 - 41
[13] A REGIOCHEMICAL CONTROL IN THE PI-ALLYLPALLADIUM SUBSTITUTION - PREPARATION OF OPTICALLY-ACTIVE GAMMA-SILYLALLYLAMINES
INAMI, H
ITO, T
URABE, H
SATO, F
[J]. TETRAHEDRON LETTERS, 1993, 34 (37) : 5919 - 5922
[14] PALLADIUM-CATALYZED IMINOCARBONYLATIVE CROSS-COUPLING REACTION BETWEEN HALOARENES, T-BUNC, AND 9-ALKYL-9-BBN DERIVATIVES - SYNTHESIS OF ALKYL ARYL KETONES
ISHIYAMA, T
OHE, T
MIYAURA, N
SUZUKI, A
[J]. TETRAHEDRON LETTERS, 1992, 33 (31) : 4465 - 4468
[15] Synthetic studies and mechanistic insight in nickel-catalyzed [4+2+1] cycloadditions
Ni, Y
Montgomery, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) : 2609 - 2614
[16] PALLADIUM-CATALYZED DOUBLE CARBONYLATION OF ARYL HALIDES TO GIVE ALPHA-KETO AMIDES - MECHANISTIC STUDIES
OZAWA, F
SOYAMA, H
YANAGIHARA, H
AOYAMA, I
TAKINO, H
IZAWA, K
YAMAMOTO, T
YAMAMOTO, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (11) : 3235 - 3245
[17] Synthesis and reactivity of four-membered azapalladacycles derived from N,N-dialkyl-2-iodoanilines:: Insertion reactions of carbenes into the carbon-palladium bond
Solé, D
Vallverdú, L
Solans, X
Font-Bardia, M
Bonjoch, J
[J]. ORGANOMETALLICS, 2004, 23 (06) : 1438 - 1447
[18] New insights into the mechanism of palladium-catalyzed allylic amination
Watson, IDG
Yudin, AK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (49) : 17516 - 17529
[19] Simple, efficient catalyst system for the palladium-catalyzed amination of aryl chlorides, bromides, and triflates
Wolfe, JP
Tomori, H
Sadighi, JP
Yin, JJ
Buchwald, SL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (04) : 1158 - 1174

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