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

Meng Juan Zhang, Hong Xi Li, David J. Young, Hai Yan Li, Jian Ping Lang

Research output: Contribution to journalArticleResearchpeer-review

Abstract

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.

Original languageEnglish
Pages (from-to)3567-3574
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume17
Issue number14
DOIs
Publication statusPublished - 14 Apr 2019

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cross coupling
Nickel
alcohols
Alcohols
nickel
Dehydrogenation
Ketones
dehydrogenation
ketones
Quinolines
Catalysts
catalysts
quinoline
selectivity
Substrates
methodology
products

Cite this

Zhang, Meng Juan ; Li, Hong Xi ; Young, David J. ; Li, Hai Yan ; Lang, Jian Ping. / Reaction condition controlled nickel(ii)-catalyzed C-C cross-coupling of alcohols. In: Organic and Biomolecular Chemistry. 2019 ; Vol. 17, No. 14. pp. 3567-3574.
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Reaction condition controlled nickel(ii)-catalyzed C-C cross-coupling of alcohols. / Zhang, Meng Juan; Li, Hong Xi; Young, David J.; Li, Hai Yan; Lang, Jian Ping.

In: Organic and Biomolecular Chemistry, Vol. 17, No. 14, 14.04.2019, p. 3567-3574.

Research output: Contribution to journalArticleResearchpeer-review

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