Palladium-catalyzed 2-pyridylmethyl transfer from 2-(2-pyridyl)-ethanol derivatives to organic halides by chelation-assisted cleavage of unstrained Csp3-Csp3 bonds

被引：108

作者：

Niwa, Takashi ^{[1
]}

Yorimitsu, Hideki ^{[1
]}

Oshima, Koichiro ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Nishikyo Ku, Kyoto 6158510, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 15期

关键词：

azaarenes; C-C activation; cross-coupling; homogeneous catalysis; palladium;

D O I：

10.1002/anie.200604472

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Making a break for it: Treatment of 2-(2-pyridyl)ethanol derivatives with aryl chlorides in the presence of a palladium catalyst results in the transfer of the pyridylmethyl moiety of the alcohol to yield the corresponding (2-pyridyl-methyl)arene. The reaction proceeds by chelation-assisted cleavage of an Csp3-C5p3 bond (see scheme) followed by formation of a carbon-carbon bond. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：2643 / 2645

页数：3

共 32 条

[1] Alkali metal and magnesium enamides from metallation of the alkyl ligands [(2-Pyr)(SiMe3)CH2] and [6-Me-(2-Pyr)(SiMe3)CH2]:: a solid state and ab initio study [J].

Andrews, PC ;

Armstrong, DR ;

Raston, CL ;

Roberts, BA ;

Skelton, BW ;

White, AH .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2001, (07) :996-1006

[2]

[Anonymous], 1999, ANGEW CHEM, V111, P918

[3] TRANSITION-METAL CATALYZED REARRANGEMENTS OF SMALL RING ORGANIC-MOLECULES [J].

BISHOP, KC .

CHEMICAL REVIEWS, 1976, 76 (04) :461-486

[4] Catalytic multistep reactions via palladacycles [J].

Catellani, M .

SYNLETT, 2003, (03) :298-313

[5] Ru3(CO)12-catalyzed decarbonylative cleavage of a C-C bond of alkyl phenyl ketones [J].

Chatani, N ;

Ie, Y ;

Kakiuchi, F ;

Murai, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (37) :8645-8646

[6] A highly selective synthesis of diarylethynes and their oligomers by a palladium-catalyzed Sonogashira coupling reaction under phase transfer conditions [J].

Chow, HF ;

Wan, CW ;

Low, KH ;

Yeung, YY .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (05) :1910-1913

[7] THE ORGANOMETALLIC CHEMISTRY OF ALKANES [J].

CRABTREE, RH .

CHEMICAL REVIEWS, 1985, 85 (04) :245-269

[8] Synthesis of doubly unsaturated aldehydes and ketones by a novel beta-decarbopalladation [J].

Harayama, H ;

Kuroki, T ;

Kimura, M ;

Tanaka, S ;

Tamaru, Y .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (21) :2352-2354

[9]

Harayama H., 1997, ANGEW CHEM, V109, P2449

[10] Palladium-catalyzed stereo- and regiospecific allylation of aryl halides with homoallyl alcohols via retro-allylation:: Selective generation and use of σ-allylpalladium [J].

Hayashi, S ;

Hirano, K ;

Yorimitsu, H ;

Oshima, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) :2210-2211

← 1 2 3 4 →