Palladium-Catalyzed Cross Coupling Reaction of Benzyl Bromides with Diazoesters for Stereoselective Synthesis of (E)-α,β-Diarylacrylates

被引：92

作者：

Yu, Wing-Yiu ^{[1
]}

Tsoi, Yuk-Tai

Zhou, Zhongyuan

Chan, Albert S. C.

机构：

[1] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Kowloon, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 02期

关键词：

C-H INSERTION; ALPHA-DIAZOCARBONYL COMPOUNDS; CARBENE INSERTION; BIOLOGICAL EVALUATION; HECK REACTION; COMPLEXES; CYCLOPROPANATION; HALIDES; BOND; FUNCTIONALIZATION;

D O I：

10.1021/ol8026076

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Pd-catalyzed cross-coupling reaction of benzyl bromides with alpha-aryldiazoesters is described, and E-alpha,beta-diarylacrylates were obtained in good yields and excellent E-to-Z selectivity (>20:1).

引用

页码：469 / 472

页数：4

共 41 条

[31] YLIDE FORMATION FROM THE REACTION OF CARBENES AND CARBENOIDS WITH HETEROATOM LONE PAIRS
PADWA, A
HORNBUCKLE, SF
[J]. CHEMICAL REVIEWS, 1991, 91 (03) : 263 - 309
[32] Palladium-catalyzed cross-coupling of α-diazocarbonyl compounds with arylboronic acids
Peng, Cheng
Wang, Yan
Wang, Jianbo
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (05) : 1566 - +
[33] 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
[34] Stuart DR, 2007, SCIENCE, V316, P1172, DOI 10.1126/science.1141956
[35] Suzuki A., 2002, MODERN ARENE CHEM, P53, DOI DOI 10.1002/3527601767.CH3
[36] Intermolecular amidation of unactivated sp2 and sp3 C-H bonds via palladium-catalyzed cascade C-H activation/nitrene insertion
Thu, Hung-Yat
Yu, Wing-Yiu
Che, Chi-Ming
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (28) : 9048 - 9049
[37] Tsuji J., 1995, PALLADIUM REAGENTS C
[38] Palladium-catalyzed oxidative ethoxycarbonylation of aromatic C-H bond with diethyl azodicarboxylate
Yu, Wing-Yiu
Sit, Wing Nga
Lai, Kin-Man
Zhou, Zhongyuan
Chan, Albert S. C.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (11) : 3304 - +
[39] OVERLAP CONTROL OF CARBANIONOID REACTIONS .2. THE STEROCHEMISTRY OF THE PERKIN REACTION AND RELATED CONDENSATION REACTIONS
ZIMMERMAN, HE
AHRAMJIAN, L
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (09) : 2086 - 2091
[40] Zollinger H., 1994, DIAZO CHEM, V1

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