Nickel-Catalyzed One-Pot Suzuki-Miyaura Cross-Coupling of Phenols and Arylboronic Acids Mediated by N,N-Ditosylaniline

被引：16

作者：

Chen, Liangshun ^{[1
,2
]}

Lang, Hongyue ^{[1
,2
]}

Fang, Lei ^{[1
,2
]}

Zhu, Mengyun ^{[1
,2
]}

Liu, Jinqian ^{[1
,2
]}

Yu, Jianjun ^{[1
,2
]}

Wang, Limin ^{[1
,2
]}

机构：

[1] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China

[2] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 23期

关键词：

Nickel; Chemoselectivity; Boronic acids; Biaryls; Cross-coupling; BOND FORMATION; DIRECT ARYLATION; PALLADIUM; ACTIVATION; AMINATION; 4-HYDROXYCOUMARINS; ELECTROPHILES; EFFICIENT; HALIDES; SALTS;

D O I：

10.1002/ejoc.201402475

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for the construction of two distinct C-aryl-C-aryl bonds through the Ni-catalyzed Suzuki-Miyaura cross-coupling of phenols with arylboronic acids has been developed. This reaction proceeds through the in situ tosylation of phenols by using N,N-ditosylaniline as the sulfonylating reagent, which is highly active, markedly stable, and easily prepared. The scope with respect to the coupling partners-phenols and boronic acids - is broad, and sensitive functional groups are tolerated. Phenols, especially those containing an unprotected amino group, which are generally problematic for coupling under conventional one-pot conditions, are also viable substrates in this transformation.

引用

页码：4953 / 4957

页数：5

共 58 条

[1] Dehydrative Direct Arylations of Arenes with Phenols via Ruthenium-Catalyzed C-H and C-OH Bond Functionalizations [J].

Ackermann, Lutz ;

Mulzer, Michael .

ORGANIC LETTERS, 2008, 10 (21) :5043-5045

[2] Well-Defined Ruthenium(II) Carboxylate as Catalyst for Direct C-H/C-O Bond Arylations with Phenols in Water [J].

Ackermann, Lutz ;

Pospech, Jola ;

Potukuchi, Harish Kumar .

ORGANIC LETTERS, 2012, 14 (08) :2146-2149

[3] Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: a critical overview. Part 2: The Suzuki reaction [J].

Alonso, Francisco ;

Beletskaya, Irina P. ;

Yus, Miguel .

TETRAHEDRON, 2008, 64 (14) :3047-3101

[4]

[Anonymous], ANGEW CHEM

[5] Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances [J].

Bellina, F ;

Carpita, A ;

Rossi, R .

SYNTHESIS-STUTTGART, 2004, (15) :2419-2440

[6] The first Suzuki cross-couplings of aryltrimethylammonium salts [J].

Blakey, SB ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (20) :6046-6047

[7] Biaryl Formation Involving Carbon-Based Leaving Groups: Why Not? [J].

Bonesi, Sergio M. ;

Fagnoni, Maurizio ;

Albini, Angelo .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (52) :10022-10025

[8] An efficient and cost-effective synthesis of 2-phenyl-3-aminopyridine [J].

Caron, S ;

Massett, SS ;

Bogle, DE ;

Castaldi, MJ ;

Braish, TF .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2001, 5 (03) :254-256

[9] A General Regioselective Synthesis of 2,4-Diarylpyrimidines from 2-Thiouracil through Two Orthogonal Cross-Coupling Reactions [J].

Cernova, Miroslava ;

Pohl, Radek ;

Klepetarova, Blanka ;

Hocek, Michal .

SYNLETT, 2012, (09) :1305-1308

[10] Nickel-Catalyzed Cross-Coupling of Phenols and Arylboronic Acids Through an In Situ Phenol Activation Mediated by PyBroP [J].

Chen, Guo-Jun ;

Huang, Jie ;

Gao, Lian-Xun ;

Han, Fu-She .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (14) :4038-4042

← 1 2 3 4 5 6 →