Palladium-Catalyzed Decarboxylative Arylation of C-H Bonds by Aryl Acylperoxides

被引：175

作者：

Yu, Wing-Yiu ^{[1
]}

Sit, Wing Nga

Zhou, Zhongyuan

Chan, Albert S. -C.

机构：

[1] Hong Kong Polytech Univ, Open Lab Chirotechnol, Inst Mol Technol Drug Discovery & Synth, Kowloon, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 15期

关键词：

CROSS-COUPLING REACTION; BIARYL SYNTHESIS; AROMATIC CARBOXYLATES; BENZOIC-ACIDS; PD; FUNCTIONALIZATION; ACTIVATION; COMPLEXES; INSERTION; HALIDES;

D O I：

10.1021/ol900756g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Pd(OAC)(2)-catalyzed protocol for decarboxylative arylation of aromatic C-H bond was developed using aryl acylperoxides as inexpensive aryl sources. Substrates containing pyridyl, oxime, and oxazoline groups undergo effectively ortho-selective C-H arylation with excellent functional group tolerance. This arylation should begin by directing-group-assisted cyclopalladation, followed by the reaction of the palladacycle with aryl radicals generated in situ by thermal decomposition of the peroxides.

引用

页码：3174 / 3177

页数：4

共 47 条

[1] Catalytic arylation reactions by C-H bond activation with aryl tosylates
Ackermann, L
Althammer, A
Born, R
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) : 2619 - 2622
[2] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation
Alberico, Dino
Scott, Mark E.
Lautens, Mark
[J]. CHEMICAL REVIEWS, 2007, 107 (01) : 174 - 238
[3] Biaryl synthesis via decarboxylative Pd-catalyzed reactions of arenecarboxylic acids and diaryliodonium triflates
Becht, Jean-Michel
Le Drian, Claude
[J]. ORGANIC LETTERS, 2008, 10 (14) : 3161 - 3164
[4] Synthesis of biaryls via decarboxylative Pd-catalyzed cross-coupling reaction
Becht, Jean-Michel
Catala, Cedric
Le Drian, Claude
Wagner, Alain
[J]. ORGANIC LETTERS, 2007, 9 (09) : 1781 - 1783
[5] The Copper-Catalyzed Decarboxylative Coupling of the sp3-Hybridized Carbon Atoms of α-Amino Acids
Bi, Hai-Peng
Zhao, Liang
Liang, Yong-Min
Li, Chao-Jun
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (04) : 792 - 795
[6] Biaryl Formation Involving Carbon-Based Leaving Groups: Why Not?
Bonesi, Sergio M.
Fagnoni, Maurizio
Albini, Angelo
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (52) : 10022 - 10025
[7] Twofold C-H functionalization:: Palladium-catalyzed ortho arylation of anilides
Brasche, Gordon
Garcia-Fortanet, Jorge
Buchwald, Stephen L.
[J]. ORGANIC LETTERS, 2008, 10 (11) : 2207 - 2210
[8] Oxidation of complexes by (O2CPh)2 and (ER)2 (E = S, Se), including structures of Pd(CH2CH2CH2CH2)(SePh)2(bpy) (bpy = 2,2′-bipyridine) and MMe2(SePh)2(L2) (M = Pd, Pt; L2 = bpy, 1,10-phenanthroline) and C•••O and C•••E bond formation at palladium(IV)
Canty, AJ
Jin, H
Skelton, BW
White, AH
[J]. INORGANIC CHEMISTRY, 1998, 37 (16) : 3975 - 3981
[9] Ruthenium porphyrin catalyzed intramolecular carbenoid C-H insertion. Stereloselective synthesis of cis-disubstituted oxygen and nitrogen heterocycles
Cheung, WH
Zheng, SL
Yu, WY
Zhou, GC
Che, CM
[J]. ORGANIC LETTERS, 2003, 5 (14) : 2535 - 2538
[10] Two methods for direct ortho-arylation of benzoic acids
Chiong, Hendrich A.
Pham, Quynh-Nhu
Daugulis, Olafs
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (32) : 9879 - 9884

← 1 2 3 4 5 →