Direct benzylic alkylation via Ni-catalyzed selective benzylic sp3 C-O activation

被引：168

作者：

Guan, Bing-Tao ^{[1
,2
]}

Xiang, Shi-Kai ^{[1
,2
,3
]}

Wang, Bi-Qin ^{[1
,2
,3
]}

Sun, Zuo-Peng ^{[1
,2
,3
]}

Wang, Yang ^{[4
]}

Zhao, Ke-Qing ^{[3
]}

Shi, Zhang-Jie ^{[1
,2
,5
]}

机构：

[1] Peking Univ, Coll Chem, Minist Educ, Beijing Natl Lab Mol Sci, Beijing 100871, Peoples R China

[2] Peking Univ, Coll Chem, Minist Educ, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China

[3] Sichuan Normal Univ, Coll Chem & Mat Sci, Chengdu 410066, Sichuan, Peoples R China

[4] China Agr Univ, Dept Chem, Beijing 100094, Peoples R China

[5] Chinese Acad Sci, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 11期

关键词：

D O I：

10.1021/ja710944j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This article demonstrates the first cross coupling of benzyl ether with Grignard reagents via Ni-catalyzed benzylic sp(3) C-O activation with high efficiency and excellent chemoselectivity. Benzylic sp(3) C-O and aryl sp(2) C-O were differentiated, controlled by ligands.

引用

页码：3268 / +

页数：3

共 27 条

[1] Nickel(0)-catalyzed asymmetric cross-coupling reactions of allylic compounds with arylboronic acids
Chung, KG
Miyake, Y
Uemura, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (01): : 15 - 18
[2] CORRIU JP, 1972, J CHEM SOC CHEM COMM, P144
[3] Nickel-catalyzed cross-coupling of aryl Grignard reagents with aromatic alkyl ethers: An efficient synthesis of unsymmetrical biaryls
Dankwardt, JW
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (18) : 2428 - 2432
[4] Diederich F., 1998, METAL CATALYZED CROS, DOI DOI 10.1002/9783527612222
[5] Catalysts for cross-coupling reactions with non-activated alkyl halides
Frisch, AC
Beller, M
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (05) : 674 - 688
[6] Methylation of arenes via Ni-catalyzed aryl C-O/F activation
Guan, Bing-Tao
Xiang, Shi-Kai
Wu, Tao
Sun, Zuo-Peng
Wang, Bi-Qin
Zhao, Ke-Qing
Shi, Zhang-Jie
[J]. CHEMICAL COMMUNICATIONS, 2008, (12) : 1437 - 1439
[7] NICKEL-CATALYZED CROSS-COUPLING OF ARYL PHOSPHATES WITH GRIGNARD AND ORGANO-ALUMINUM REAGENTS - SYNTHESIS OF ALKYLBENZENES, ALKENYLBENZENES AND ARYLBENZENES FROM PHENOLS
HAYASHI, T
KATSURO, Y
OKAMOTO, Y
KUMADA, M
[J]. TETRAHEDRON LETTERS, 1981, 22 (44) : 4449 - 4452
[8] Ruthenium-catalyzed functionalization of aryl carbon-oxygen bonds in aromatic ethers with organoboron compounds
Kakiuchi, F
Usui, M
Ueno, S
Chatani, N
Murai, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (09) : 2706 - 2707
[9] A highly effective (triphenyl phosphite)palladium catalyst for a cross-coupling reaction of allylic alcohols with organoboronic acids
Kayaki, Y
Koda, T
Ikariya, T
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (24) : 4989 - 4993
[10] Pd-catalyzed C3-selective allylation of indoles with allyl alcohols promoted by triethylborane
Kimura, M
Futamata, M
Mukai, R
Tamaru, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) : 4592 - 4593

← 1 2 3 →