Ir-catalyzed functionalization of 2-substituted indoles at the 7-position: Nitrogen-directed aromatic borylation

被引：223

作者：

Paul, Sulagna ^{[1
]}

Chotana, Ghayoor A. ^{[1
]}

Holmes, Daniel ^{[1
]}

Reichle, Rebecca C. ^{[1
]}

Maleczka, Robert E., Jr. ^{[1
]}

Smith, Milton R., III ^{[1
]}

机构：

[1] Michigan State Univ, Dept Chem, E Lansing, MI 48824 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 49期

关键词：

D O I：

10.1021/ja0631652

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ir-catalyzed borylation of 2-substituted indoles selectively yields 7-borylated products in good yields. N-Protection, required for previous functionalizations of 2-substituted indoles, is unnecessary. Copyright © 2006 American Chemical Society.

引用

页码：15552 / 15553

页数：2

共 28 条

[21] Arylboronic acids and arylpinacolboronate esters in Suzuki coupling reactions involving indoles.: Partner role swapping and heterocycle protection [J].

Prieto, M ;

Zurita, E ;

Rosa, E ;

Muñoz, L ;

Lloyd-Williams, P ;

Giralt, E .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (20) :6812-6820

[22]

STROH R, 1959, LIEBIGS ANN CHEM, V623, P176

[23]

SUNDBERG RJ, 1984, COMPREHENSIVE HETERO, V4, P314

[24] Iridium-catalyzed C-H coupling reaction of heteroaromatic compounds with bis(pinacolato)diboron: regioselective synthesis of heteroarylboronates [J].

Takagi, J ;

Sato, K ;

Hartwig, JF ;

Ishiyama, T ;

Miyaura, N .

TETRAHEDRON LETTERS, 2002, 43 (32) :5649-5651

[25] Regioselective aromatic borylation in an inert solvent [J].

Tse, MK ;

Cho, JY ;

Smith, MR .

ORGANIC LETTERS, 2001, 3 (18) :2831-2833

[26] Direct C-arylation of free (NH)-indoles and pyrroles catalyzed by Ar-Rh(III) complexes assembled in situ [J].

Wang, X ;

Lane, BS ;

Sames, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (14) :4996-4997

[27] Beyond thermodynamic acidity: A perspective on the complex-induced proximity effect (CIPE) in deprotonation reactions [J].

Whisler, MC ;

MacNeil, S ;

Snieckus, V ;

Beak, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (17) :2206-2225

[28] DETECTION OF A NEW CHLOROPEROXIDASE IN PSEUDOMONAS-PYRROCINIA [J].

WIESNER, W ;

VANPEE, KH ;

LINGENS, F .

FEBS LETTERS, 1986, 209 (02) :321-324

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