Tris(pyrazolyl)borate Cobalt-Catalyzed Hydrogenation of C=O, C=C, and C=N Bonds: An Assistant Role of a Lewis Base

Yang Lin; De Ping Zhu; Yi Ran Du; Rui Zhang; Suo Jiang Zhang; Bao Hua Xu

doi:10.1021/acs.orglett.9b00679

Tris(pyrazolyl)borate Cobalt-Catalyzed Hydrogenation of C=O, C=C, and C=N Bonds: An Assistant Role of a Lewis Base

Yang Lin
, De Ping Zhu
, Yi Ran Du
, Rui Zhang^*
, Suo Jiang Zhang
, Bao Hua Xu

^*Corresponding author for this work

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

25 Citations (Scopus)

Abstract

The combination of tris(pyrazolyl)borate cobalt complexes and Lewis base is developed as an efficient catalyst precursor in the homogeneous hydrogenation. A broad substrate scope including carbonyls, alkenes, enamines, and imines is reduced with 60 atm of H ₂ at 60 °C. Mechanistic studies support the hydrogenation operates through a frustrated Lewis pair (FLP)-like reduction process. These results highlight the development of novel non-noble metal catalytic processes, when combined with the diverse small molecule activation chemistry associated with FLPs.

Original language	English
Pages (from-to)	2693-2698
Number of pages	6
Journal	Organic Letters
Volume	21
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.9b00679
Publication status	Published - 19 Apr 2019
Externally published	Yes

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title = "Tris(pyrazolyl)borate Cobalt-Catalyzed Hydrogenation of C=O, C=C, and C=N Bonds: An Assistant Role of a Lewis Base",

abstract = " The combination of tris(pyrazolyl)borate cobalt complexes and Lewis base is developed as an efficient catalyst precursor in the homogeneous hydrogenation. A broad substrate scope including carbonyls, alkenes, enamines, and imines is reduced with 60 atm of H 2 at 60 °C. Mechanistic studies support the hydrogenation operates through a frustrated Lewis pair (FLP)-like reduction process. These results highlight the development of novel non-noble metal catalytic processes, when combined with the diverse small molecule activation chemistry associated with FLPs.",

author = "Yang Lin and Zhu, \{De Ping\} and Du, \{Yi Ran\} and Rui Zhang and Zhang, \{Suo Jiang\} and Xu, \{Bao Hua\}",

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year = "2019",

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doi = "10.1021/acs.orglett.9b00679",

language = "English",

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T1 - Tris(pyrazolyl)borate Cobalt-Catalyzed Hydrogenation of C=O, C=C, and C=N Bonds

T2 - An Assistant Role of a Lewis Base

AU - Lin, Yang

AU - Zhu, De Ping

AU - Du, Yi Ran

AU - Zhang, Rui

AU - Zhang, Suo Jiang

AU - Xu, Bao Hua

PY - 2019/4/19

Y1 - 2019/4/19

N2 - The combination of tris(pyrazolyl)borate cobalt complexes and Lewis base is developed as an efficient catalyst precursor in the homogeneous hydrogenation. A broad substrate scope including carbonyls, alkenes, enamines, and imines is reduced with 60 atm of H 2 at 60 °C. Mechanistic studies support the hydrogenation operates through a frustrated Lewis pair (FLP)-like reduction process. These results highlight the development of novel non-noble metal catalytic processes, when combined with the diverse small molecule activation chemistry associated with FLPs.

AB - The combination of tris(pyrazolyl)borate cobalt complexes and Lewis base is developed as an efficient catalyst precursor in the homogeneous hydrogenation. A broad substrate scope including carbonyls, alkenes, enamines, and imines is reduced with 60 atm of H 2 at 60 °C. Mechanistic studies support the hydrogenation operates through a frustrated Lewis pair (FLP)-like reduction process. These results highlight the development of novel non-noble metal catalytic processes, when combined with the diverse small molecule activation chemistry associated with FLPs.

UR - https://www.scopus.com/pages/publications/85064341887

U2 - 10.1021/acs.orglett.9b00679

DO - 10.1021/acs.orglett.9b00679

M3 - Article

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AN - SCOPUS:85064341887

SN - 1523-7060

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SP - 2693

EP - 2698

JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

Tris(pyrazolyl)borate Cobalt-Catalyzed Hydrogenation of C=O, C=C, and C=N Bonds: An Assistant Role of a Lewis Base

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