Palladium-Catalyzed Cross-Coupling of Cyanohydrins with Aryl Bromides: Construction of Biaryl Ketones

Jadab Majhi; Bohang Zhou; Yuxin Zhuang; Mai-Jan Tom; Huifang Dai; P. Andrew Evans

doi:10.1055/a-1850-3687

Synthesis, Table of Contents

Synthesis 2023; 55(11): 1752-1763
DOI: 10.1055/a-1850-3687

paper

Special Issue dedicated to Prof. Cristina Nevado, recipient of the 2021 Dr. Margaret Faul Women in Chemistry Award

Palladium-Catalyzed Cross-Coupling of Cyanohydrins with Aryl Bromides: Construction of Biaryl Ketones

Jadab Majhi

^aDepartment of Chemistry, Queen’s University, 90 Bader Lane, Kingston, Ontario, K7L 3N6, Canada

,

Bohang Zhou

^aDepartment of Chemistry, Queen’s University, 90 Bader Lane, Kingston, Ontario, K7L 3N6, Canada

^bCollege of Chemistry and Pharmacy, Northwest A&F University, Yangling District, Xianyang, Shaanxi 712100, P. R. of China

,

Yuxin Zhuang

^aDepartment of Chemistry, Queen’s University, 90 Bader Lane, Kingston, Ontario, K7L 3N6, Canada

^cCollege of Pharmaceutical Sciences, Zhejiang University, 866 Yuhangtang Rd, Hangzhou, Zhejiang 310058, P. R. of China

,

Mai-Jan Tom

^aDepartment of Chemistry, Queen’s University, 90 Bader Lane, Kingston, Ontario, K7L 3N6, Canada

,

Huifang Dai∗

^aDepartment of Chemistry, Queen’s University, 90 Bader Lane, Kingston, Ontario, K7L 3N6, Canada

^dSchool of Pharmacy, Fudan University, 826 Zhangheng Rd, Pudong Zone, Shanghai 201203, P. R. of China

,

P. Andrew Evans ∗

^aDepartment of Chemistry, Queen’s University, 90 Bader Lane, Kingston, Ontario, K7L 3N6, Canada

^eXiangya School of Pharmaceutical Sciences, Central South University, Changsha, Hunan 410013, P. R. of China

› Author Affiliations

Abstract

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Abstract

The palladium-catalyzed cross-coupling of the lithium anion of aryl tert-butyldimethylsilyl-protected cyanohydrins with aryl bromides followed by in situ deprotection with fluoride ion provides a convenient and versatile approach to biaryl ketones. This protocol represents the first example of a palladium-catalyzed arylation of a cyanohydrin, which functions as an acyl anion equivalent. Hence, in contrast to classical cross-coupling reactions, the pronucleophile component is incorporated in the product to permit further functionalization. We then highlight the synthetic utility of the new method with applications to bioactive biaryl ketones and the construction of a triaryl diketone that has been used to prepare an extended tetrathiafulvalene.

Key words

acyl anions - aryl halides - biaryl ketones - cyanohydrins - palladium catalysis

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