Meta-Selective C-H Functionalization Using a Nitrile-Based Directing Group and Cleavable Si-Tether

被引：214

作者：

Lee, Sunggi ^{[1
]}

Lee, Hyelee ^{[1
]}

Tan, Kian L. ^{[1
]}

机构：

[1] Boston Coll, Chestnut Hill, MA 02467 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 50期

关键词：

IRIDIUM-CATALYZED BORYLATION; ELECTRON-DEFICIENT ARENES; BOND FORMATION; 1,3-DISUBSTITUTED ARENES; ORTHO-HALOGENATION; OLEFINATION; ACTIVATION; COMPLEXES; PALLADIUM; SILANOL;

D O I：

10.1021/ja4107034

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A nitrile-based template that enables metaselective C-H bond functionalization was developed. The template is applicable to a range of substituted arenes and tolerates a variety of functional groups. The directing group uses a silicon atom for attachment, allowing for a facile introduction/deprotection strategy increasing the synthetic practicality of this template.

引用

页码：18778 / 18781

页数：4

共 67 条

[1] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].

Ackermann, Lutz .

CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345

[2] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[3]

Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]

[4] Conversion of 1,3-disubstituted arenes to chiral α,α-diaryl methylammonium chlorides using arene borylation [J].

Boebel, Timothy A. ;

Hartwig, John F. .

TETRAHEDRON, 2008, 64 (29) :6824-6830

[5] Mechanistic Understanding of the Unexpected Meta Selectivity in Copper-Catalyzed Anilide C-H Bond Arylation [J].

Chen, Bo ;

Hou, Xue-Long ;

Li, Yu-Xue ;

Wu, Yun-Dong .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (20) :7668-7671

[6] A predictably selective aliphatic C-H oxidation reaction for complex molecule synthesis [J].

Chen, Mark S. ;

White, M. Christina .

SCIENCE, 2007, 318 (5851) :783-787

[7] Combined Effects on Selectivity in Fe-Catalyzed Methylene Oxidation [J].

Chen, Mark S. ;

White, M. Christina .

SCIENCE, 2010, 327 (5965) :566-571

[8]

Chernyak N., 2010, J AM CHEM SOC, V132, P8270

[9] Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds [J].

Cho, JY ;

Tse, MK ;

Holmes, D ;

Maleczka, RE ;

Smith, MR .

SCIENCE, 2002, 295 (5553) :305-308

[10] Steric and chelate directing effects in aromatic borylation [J].

Cho, JY ;

Iverson, CN ;

Smith, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) :12868-12869

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