Reaction condition controlled nickel(ii)-catalyzed C-C cross-coupling of alcohols

The challenge in the C-C cross-coupling of secondary and primary alcohols using acceptorless dehydrogenation coupling (ADC) is the difficulty in accurately controlling product selectivities. Herein, we report a controlled approach to a diverse range of β-alkylated secondary alcohols, α-alkylated ket...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2019-04, Vol.17 (14), p.3567-3574
Main Authors: Zhang, Meng-Juan, Li, Hong-Xi, Young, David J, Li, Hai-Yan, Lang, Jian-Ping
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
Alkylation
Catalysis
Catalysts
Chemical reactions
Cross coupling
Crystallography
Dehydrogenation
Ketones
Nickel
NMR
Nuclear magnetic resonance
Organic chemistry
Organic compounds
Quinolines
Substrates
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Summary:The challenge in the C-C cross-coupling of secondary and primary alcohols using acceptorless dehydrogenation coupling (ADC) is the difficulty in accurately controlling product selectivities. Herein, we report a controlled approach to a diverse range of β-alkylated secondary alcohols, α-alkylated ketones and α,β-unsaturated ketones using the ADC methodology employing a Ni(ii) 4,6-dimethylpyrimidine-2-thiolate cluster catalyst under different reaction conditions. This catalyst could tolerate a wide range of substrates and exhibited a high activity for the annulation reaction of secondary alcohols with 2-aminobenzyl alcohols to yield quinolines. This work is an example of precise chemoselectivity control by careful choice of reaction conditions.
ISSN:1477-0520
1477-0539
DOI:10.1039/C9OB00418A