Cobalt-Catalyzed C4-Selective Direct Alkylation of Pyridines

How pyridine got its tail: A new catalyst for the atom‐economical C4‐selective direct alkylation of pyridines is described. A combination of CoBr2 and LiBEt3H catalyzes the reaction of pyridines with 1‐alkenes at 70 °C to give alkylation products with C4/C2 ratios of >20:1. Substrate/catalyst rat...

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Published inAngewandte Chemie International Edition Vol. 52; no. 11; pp. 3213 - 3216
Main Authors Andou, Takashi, Saga, Yutaka, Komai, Hirotomo, Matsunaga, Shigeki, Kanai, Motomu
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 11.03.2013
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
EditionInternational ed. in English
Subjects
Alkylation
atom economy
Catalysis
Catalysts
Chemistry
Chemistry, Multidisciplinary
Cobalt - chemistry
heterocyclic compounds
Physical Sciences
Pyridines
Pyridines - chemistry
Science & Technology
synthetic methods
C-H ARYLATION
HETEROCYCLES
ELECTRON-DEFICIENT POLYFLUOROARENES
alkylation
atom economy
catalysis
OLEFINS
heterocyclic compounds
synthetic methods
ALKENYLATION
HYDROAZIDATION
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Summary:How pyridine got its tail: A new catalyst for the atom‐economical C4‐selective direct alkylation of pyridines is described. A combination of CoBr2 and LiBEt3H catalyzes the reaction of pyridines with 1‐alkenes at 70 °C to give alkylation products with C4/C2 ratios of >20:1. Substrate/catalyst ratios of up to 4000, and a turnover number of 3440 were achieved.
Bibliography:MEXT
Naito Foundation
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ArticleID:ANIE201208666
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JST
We thank Mr. Shohei Yamamoto for fruitful discussions and experimental support. This work was supported in part by ERATO from JST (M.K.), a Grant-in-Aid for Scientific Research on Innovative Areas "Molecular Activation Directed toward Straightforward Synthesis" from MEXT (S.M.), the ACT-C program from JST (S.M.) and the Naito Foundation. T.A. thanks JSPS for a postdoctoral fellowship.
We thank Mr. Shohei Yamamoto for fruitful discussions and experimental support. This work was supported in part by ERATO from JST (M.K.), a Grant‐in‐Aid for Scientific Research on Innovative Areas “Molecular Activation Directed toward Straightforward Synthesis” from MEXT (S.M.), the ACT‐C program from JST (S.M.) and the Naito Foundation. T.A. thanks JSPS for a postdoctoral fellowship.
These authors contributed equally to this work.
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ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201208666