o-(Trialkylstannyl)anilines and their utility in Migita-Kosugi-Stille cross-coupling: direct introduction of the 2-aminophenyl substituent

被引：13

作者：

Izgu, Enver Cagri ^{[1
]}

Hoye, Thomas R. ^{[1
]}

机构：

[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 37期

基金：

美国国家卫生研究院;

关键词：

Cross-coupling; Ortho-metalation; Aniline; Organostannanes; HETEROCYCLES; ANTAGONISTS; BORYLATION; DESIGN; ACID;

D O I：

10.1016/j.tetlet.2012.06.138

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed shelf- and air-stable ortho-stannylated aniline reagents that can directly be coupled with alkenyl and aryl halides via Migita-Kosugi-Stille cross-coupling. We report (i) the efficient preparation of o-(tributylstannyl)aniline (2a) and o-(trimethylstannyl)aniline (2b), (ii) the comparison of the reactivities of 2a and 2b with those of related organostannanes in cross-coupling reaction with an alkenyl halide, and (iii) the cross-coupling of 2a and 2b with a series of arylhalides and triflate. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：4938 / 4941

页数：4

共 26 条

[1] Anslyn E. V., 2006, U SCI BOOKS, P473
[2] Appukkuttan P, 2003, SYNLETT, P1204
[3] Total synthesis of (±)-rhazinal, an alkaloidal spindle toxin from Kopsia teoi
Banwell, MG
Edwards, AJ
Jolliffe, KA
Smith, JA
Hamel, E
Verdier-Pinard, P
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (02) : 296 - 305
[4] Palladium-catalyzed borylation of ortho-substituted phenyl halides and application to the one-pot synthesis of 2,2′-disubstituted biphenyls
Baudoin, O
Guénard, D
Guéritte, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) : 9268 - 9271
[5] Application of the palladium-catalyzed borylation/Suzuki coupling (BSC) reaction to the synthesis of biologically active biaryl lactams
Baudoin, O
Cesario, M
Guénard, D
Guéritte, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (04) : 1199 - 1207
[6] ON THE NATURE OF THE COPPER EFFECT IN THE STILLE CROSS-COUPLING
FARINA, V
KAPADIA, S
KRISHNAN, B
WANG, CJ
LIEBESKIND, LS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (20) : 5905 - 5911
[7] New perspectives in the cross-coupling reactions of organostannanes
Farina, V
[J]. PURE AND APPLIED CHEMISTRY, 1996, 68 (01) : 73 - 78
[8] Preparation of dimethyl (R)- and (S)-2-(2-aminophenyl)-2-hydroxyethylphosphonate from anthranilic acid
González-Morales, A
Díaz-Coutiño, D
Fernández-Zertuche, M
García-Barradas, O
Ordóñez, M
[J]. TETRAHEDRON-ASYMMETRY, 2004, 15 (03) : 457 - 463
[9] Stereoselective Synthesis of the Epicoccin Core
Gross, Ulrike
Nieger, Martin
Braese, Stefan
[J]. ORGANIC LETTERS, 2009, 11 (20) : 4740 - 4742
[10] BORON HETEROCYCLES BEARING A PERIPHERAL RESEMBLANCE TO NATURALLY-OCCURRING PURINES - DESIGN, SYNTHESES, STRUCTURES, AND PROPERTIES
GROZIAK, MP
GANGULY, AD
ROBINSON, PD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (17) : 7597 - 7605

← 1 2 3 →