Computational characterization of a complete palladium-catalyzed cross-coupling process:: The associative transmetalation in the Stille reaction

被引：65

作者：

Alvarez, R ^{[1
]}

Faza, ON ^{[1
]}

López, CS ^{[1
]}

de Lera, AR ^{[1
]}

机构：

[1] Univ Vigo, Dept Quim Organ, Vigo 36310, Spain

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 01期

关键词：

D O I：

10.1021/ol052398f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The species presumably involved in the associative ligand substitution mechanism for the Stille cross coupling of vinyl bromide and trimethylvinyl stannane with Pd(PMe3)(2)/PMe3 as catalysts in DMF (as ligand and solvent) have been structurally and energetically characterized. The cyclic four-coordinate transition state for the rate-determining transmetalation step explains the retention of configuration in the Stille coupling of chiral nonracemic alkyl stannanes.

引用

页码：35 / 38

页数：4

共 30 条

[1] Improved carbonylation of heterocyclic chlorides and electronically challenging aryl bromides
Albaneze-Walker, J
Bazaral, C
Leavey, T
Dormer, PG
Murry, JA
[J]. ORGANIC LETTERS, 2004, 6 (13) : 2097 - 2100
[2] Mechanism of the Stille reaction catalyzed by palladium ligated to arsine ligand:: PhPdl(AsPh3)(DMF) is the species reacting with vinylstannane in DMF
Amatore, C
Bahsoun, AA
Jutand, A
Meyer, G
Ntepe, AN
Ricard, L
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (14) : 4212 - 4222
[3] Theoretical insight into the C-C coupling reactions of the vinyl, phenyl, ethynyl, and methyl complexes of palladium and platinum
Ananikov, VP
Musaev, DG
Morokuma, K
[J]. ORGANOMETALLICS, 2005, 24 (04) : 715 - 723
[4] Vinyl-vinyl coupling on late transition metals through C-C reductive elimination mechanism. A computational study
Ananikov, VP
Musaev, DG
Morokuma, K
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (11) : 2839 - 2852
[5] ENERGY-ADJUSTED ABINITIO PSEUDOPOTENTIALS FOR THE 2ND AND 3RD ROW TRANSITION-ELEMENTS
ANDRAE, D
HAUSSERMANN, U
DOLG, M
STOLL, H
PREUSS, H
[J]. THEORETICA CHIMICA ACTA, 1990, 77 (02): : 123 - 141
[6] AB-INITIO ENERGY-ADJUSTED PSEUDOPOTENTIALS FOR ELEMENTS OF GROUPS 13-17
BERGNER, A
DOLG, M
KUCHLE, W
STOLL, H
PREUSS, H
[J]. MOLECULAR PHYSICS, 1993, 80 (06) : 1431 - 1441
[7] OXIDATIVE INSERTION AS FRONTSIDE S(N)2 SUBSTITUTION - A THEORETICAL-STUDY OF THE MODEL REACTION SYSTEM PD+CH3CL
BICKELHAUPT, FM
ZIEGLER, T
SCHLEYER, PV
[J]. ORGANOMETALLICS, 1995, 14 (05) : 2288 - 2296
[8] Computational characterization of the role of the base in the Suzuki-Miyaura cross-coupling reaction
Braga, AAC
Morgon, NH
Ujaque, G
Maseras, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) : 9298 - 9307
[9] CARBON CARBON BOND FORMATION THROUGH ORGANOMETALLIC ELIMINATION-REACTIONS
BROWN, JM
COOLEY, NA
[J]. CHEMICAL REVIEWS, 1988, 88 (07) : 1031 - 1046
[10] On the configuration resulting from oxidative addition of RX to Pd(PPh3)4 and the mechanism of the cis-to-trans isomerization of [PdRX(PPh3)2] complexes (R equals aryl, X equals halide)
Casado, AL
Espinet, P
[J]. ORGANOMETALLICS, 1998, 17 (05) : 954 - 959

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