Hydrosilane Reduction of Nitriles to Primary Amines by Cobalt-Isocyanide Catalysts

Atsushi Sanagawa; Hideo Nagashima

doi:10.1021/acs.orglett.8b03736

Hydrosilane Reduction of Nitriles to Primary Amines by Cobalt-Isocyanide Catalysts

Atsushi Sanagawa, Hideo Nagashima

Department of Applied Molecular Chemistry

Research output: Contribution to journal › Article › peer-review

27 Citations (Scopus)

Abstract

Reduction of nitriles to silylated primary amines was achieved by combination of 1,1,3,3-tetramethyldisiloxane (TMDS) as the hydrosilane and a catalytic amount of Co(OPIV) ₂ (PIV = CO ^t Bu) associated with isocyanide ligands. The resulting silylated amines were subjected to acid hydrolysis or treatment with acid chlorides to give the corresponding primary amines or imides in good yields. One-pot synthesis of primary amides to primary amines with hydrosilanes was also achieved by iron-cobalt dual catalyst systems.

Original language	English
Pages (from-to)	287-291
Number of pages	5
Journal	Organic letters
Volume	21
Issue number	1
DOIs	https://doi.org/10.1021/acs.orglett.8b03736
Publication status	Published - Jan 4 2019

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.8b03736

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title = "Hydrosilane Reduction of Nitriles to Primary Amines by Cobalt-Isocyanide Catalysts",

abstract = " Reduction of nitriles to silylated primary amines was achieved by combination of 1,1,3,3-tetramethyldisiloxane (TMDS) as the hydrosilane and a catalytic amount of Co(OPIV) 2 (PIV = CO t Bu) associated with isocyanide ligands. The resulting silylated amines were subjected to acid hydrolysis or treatment with acid chlorides to give the corresponding primary amines or imides in good yields. One-pot synthesis of primary amides to primary amines with hydrosilanes was also achieved by iron-cobalt dual catalyst systems.",

author = "Atsushi Sanagawa and Hideo Nagashima",

note = "Funding Information: This work was supported by Grand-in-Aid for Scientific Research (B) (No. 18H01980) from Japan Society for the Promotion of Science. The authors are grateful to Ms. Yoshiko Kusumori (Kyushu University) for experimental assistance. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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doi = "10.1021/acs.orglett.8b03736",

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T1 - Hydrosilane Reduction of Nitriles to Primary Amines by Cobalt-Isocyanide Catalysts

AU - Sanagawa, Atsushi

AU - Nagashima, Hideo

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N2 - Reduction of nitriles to silylated primary amines was achieved by combination of 1,1,3,3-tetramethyldisiloxane (TMDS) as the hydrosilane and a catalytic amount of Co(OPIV) 2 (PIV = CO t Bu) associated with isocyanide ligands. The resulting silylated amines were subjected to acid hydrolysis or treatment with acid chlorides to give the corresponding primary amines or imides in good yields. One-pot synthesis of primary amides to primary amines with hydrosilanes was also achieved by iron-cobalt dual catalyst systems.

AB - Reduction of nitriles to silylated primary amines was achieved by combination of 1,1,3,3-tetramethyldisiloxane (TMDS) as the hydrosilane and a catalytic amount of Co(OPIV) 2 (PIV = CO t Bu) associated with isocyanide ligands. The resulting silylated amines were subjected to acid hydrolysis or treatment with acid chlorides to give the corresponding primary amines or imides in good yields. One-pot synthesis of primary amides to primary amines with hydrosilanes was also achieved by iron-cobalt dual catalyst systems.

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Hydrosilane Reduction of Nitriles to Primary Amines by Cobalt-Isocyanide Catalysts

Abstract

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