Reaction condition controlled nickel(ii)-catalyzed C–C cross-coupling of alcohols. Issue 14 (22nd March 2019)

• Record Type: Journal Article
• Authors: Zhang, Meng-Juan; Li, Hong-Xi; Young, David J.; Li, Hai-Yan; Lang, Jian-Ping
• Is Part Of: Organic & biomolecular chemistry. Volume 17:Issue 14(2019)
• Page Start: 3567
• Page End: 3574
• Publication Date: 2019-03-22
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob00418a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Nickel(ii )-catalyzed C–C cross-coupling of secondary and primary alcohols selectively produced β-alkylated secondary alcohols, α-alkylated ketones and α, β-unsaturated ketones. 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.