Cobalt-Catalyzed Chemoselective Transfer Hydrogenation of C=C and C=O Bonds with Alkanols

Biao Lin Jiang; Shuang Shuang Ma; Meng Liang Wang; Dian Sheng Liu; Bao Hua Xu; Suo Jiang Zhang

doi:10.1002/cctc.201900010

Cobalt-Catalyzed Chemoselective Transfer Hydrogenation of C=C and C=O Bonds with Alkanols

Biao Lin Jiang
, Shuang Shuang Ma
, Meng Liang Wang
, Dian Sheng Liu
, Bao Hua Xu^*
, Suo Jiang Zhang

^*Corresponding author for this work

Shanxi University
On leave to Institution of Process Engineering
Chinese Academy of Sciences
University of Chinese Academy of Sciences

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

32 Citations (Scopus)

Abstract

An environmentally benign protocol of chemoselective transfer hydrogenation of C=C and C=O bonds with alkanols under base-free conditions is developed by this study, wherein the cobalt- bidentate phosphine catalyst precursor is commercially available and the active low-valent Co species could be generated in-situ. For the conjugation enones, the vinyl group is selectively reduced, whereas with nonconjugated alkenones, the selectivity is changed to the carbonyl group. Besides, ortho-alkenyl-benzaldehydes/imines are well tolerated, and the reduction solely occurs at the C=O/C=N site with this protocol.

Original language	English
Pages (from-to)	1701-1706
Number of pages	6
Journal	ChemCatChem
Volume	11
Issue number	6
DOIs	https://doi.org/10.1002/cctc.201900010
Publication status	Published - 20 Mar 2019
Externally published	Yes

Keywords

bidentate ligand
chemoselective reduction
cobalt complex
homogeneous catalysis
transfer hydrogenation

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10.1002/cctc.201900010

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title = "Cobalt-Catalyzed Chemoselective Transfer Hydrogenation of C=C and C=O Bonds with Alkanols",

abstract = "An environmentally benign protocol of chemoselective transfer hydrogenation of C=C and C=O bonds with alkanols under base-free conditions is developed by this study, wherein the cobalt- bidentate phosphine catalyst precursor is commercially available and the active low-valent Co species could be generated in-situ. For the conjugation enones, the vinyl group is selectively reduced, whereas with nonconjugated alkenones, the selectivity is changed to the carbonyl group. Besides, ortho-alkenyl-benzaldehydes/imines are well tolerated, and the reduction solely occurs at the C=O/C=N site with this protocol.",

keywords = "bidentate ligand, chemoselective reduction, cobalt complex, homogeneous catalysis, transfer hydrogenation",

author = "Jiang, \{Biao Lin\} and Ma, \{Shuang Shuang\} and Wang, \{Meng Liang\} and Liu, \{Dian Sheng\} and Xu, \{Bao Hua\} and Zhang, \{Suo Jiang\}",

note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2019",

month = mar,

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doi = "10.1002/cctc.201900010",

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TY - JOUR

T1 - Cobalt-Catalyzed Chemoselective Transfer Hydrogenation of C=C and C=O Bonds with Alkanols

AU - Jiang, Biao Lin

AU - Ma, Shuang Shuang

AU - Wang, Meng Liang

AU - Liu, Dian Sheng

AU - Xu, Bao Hua

AU - Zhang, Suo Jiang

PY - 2019/3/20

Y1 - 2019/3/20

N2 - An environmentally benign protocol of chemoselective transfer hydrogenation of C=C and C=O bonds with alkanols under base-free conditions is developed by this study, wherein the cobalt- bidentate phosphine catalyst precursor is commercially available and the active low-valent Co species could be generated in-situ. For the conjugation enones, the vinyl group is selectively reduced, whereas with nonconjugated alkenones, the selectivity is changed to the carbonyl group. Besides, ortho-alkenyl-benzaldehydes/imines are well tolerated, and the reduction solely occurs at the C=O/C=N site with this protocol.

AB - An environmentally benign protocol of chemoselective transfer hydrogenation of C=C and C=O bonds with alkanols under base-free conditions is developed by this study, wherein the cobalt- bidentate phosphine catalyst precursor is commercially available and the active low-valent Co species could be generated in-situ. For the conjugation enones, the vinyl group is selectively reduced, whereas with nonconjugated alkenones, the selectivity is changed to the carbonyl group. Besides, ortho-alkenyl-benzaldehydes/imines are well tolerated, and the reduction solely occurs at the C=O/C=N site with this protocol.

KW - bidentate ligand

KW - chemoselective reduction

KW - cobalt complex

KW - homogeneous catalysis

KW - transfer hydrogenation

UR - https://www.scopus.com/pages/publications/85062350749

U2 - 10.1002/cctc.201900010

DO - 10.1002/cctc.201900010

M3 - Article

AN - SCOPUS:85062350749

SN - 1867-3880

VL - 11

SP - 1701

EP - 1706

JO - ChemCatChem

JF - ChemCatChem

IS - 6

ER -

Cobalt-Catalyzed Chemoselective Transfer Hydrogenation of C=C and C=O Bonds with Alkanols

Abstract

Keywords

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