Catalytic 1,4-Selective Hydrosilylation of Pyridines and Benzannulated Congeners

被引：101

作者：

Koenigs, C. David F. ^{[1
]}

Klare, Hendrik F. T. ^{[1
]}

Oestreich, Martin ^{[1
]}

机构：

[1] Tech Univ Berlin, Inst Chem, D-10623 Berlin, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 38期

关键词：

homogeneous catalysis; hydrosilylation; N-heterocycles; regioselectivity; SiH bond activation; TRANSFER HYDROGENATION; PARTIAL REDUCTION; HANTZSCH ESTERS; DIHYDROPYRIDINES; CHEMISTRY; ANILINES; IMINES; BASE;

D O I：

10.1002/anie.201305028

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Radically different! The hydrosilylation of pyridines and quinolines is strictly 1,4-selective and likely involves an ionic one-step rather than the established radical two-step hydride transfer from a ruthenium(II) hydride complex onto the respective pyridinium and quinolinium ion intermediates (see scheme; ArF=3,5-(CF3)2C6H 3). Even 4-substituted substrates react highly regioselectively. Isoquinolines yield the 1,2-reduced heterocycles. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：10076 / 10079

页数：4

共 43 条

[1]

[Anonymous], 1998, ANGEW CHEM, V110, P3314

[2] Magnesium-Catalyzed Hydroboration of Pyridines [J].

Arrowsmith, Merle ;

Hill, Michael S. ;

Hadlington, Terrance ;

Kociok-Koehn, Gabriele ;

Weetman, Catherine .

ORGANOMETALLICS, 2011, 30 (21) :5556-5559

[3] PREPARATION OF SOME N-SUBSTITUTED 1,4-DIHYDROPYRIDINES BY METAL-AMMONIA REACTIONS [J].

BIRCH, AJ ;

KARAKHANOV, EA .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (12) :480-481

[4] 2-CYCLOHEXENONES FROM 2-METHYLPYRIDINES [J].

BIRCH, AJ .

JOURNAL OF THE CHEMICAL SOCIETY, 1947, (SEP) :1270-1270

[5] Biomimetic Asymmetric Hydrogenation: In Situ Regenerable Hantzsch Esters for Asymmetric Hydrogenation of Benzoxazinones [J].

Chen, Qing-An ;

Chen, Mu-Wang ;

Yu, Chang-Bin ;

Shi, Lei ;

Wang, Duo-Sheng ;

Yang, Yan ;

Zhou, Yong-Gui .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (41) :16432-16435

[6] DIHYDROPHYRIDINES FROM SILYLATION OF PYRIDINES [J].

COOK, NC ;

LYONS, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (14) :3396-&

[7] 1,4-DIHYDROPYRIDINE [J].

COOK, NC ;

LYONS, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (14) :3283-&

[8] READY SYNTHESIS OF (+/-)-D-HOMO-OESTRONE [J].

DANISHEF.S ;

NAGEL, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (07) :373-&

[9] Partial reduction of electron-deficient pyridines [J].

Donohoe, TJ ;

McRiner, AJ ;

Sheldrake, P .

ORGANIC LETTERS, 2000, 2 (24) :3861-3863

[10] Use of dissolving metals in the partial reduction of pyridines: formation of 2-alkyl-1,2-dihydropyridines [J].

Donohoe, TJ ;

McRiner, AJ ;

Helliwell, M ;

Sheldrake, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (12) :1435-1445

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