Regio- and enantioselective umpolung gem-difluoroallylation of hydrazones via palladium catalysis enabled by N-heterocyclic carbene ligand

Shuai Huang; Fei-Fei Tong; Da-Chang Bai; Gao-Peng Zhang; Yang-Jie Jiang; Bo Zhang; Xuebing Leng; Ying-Long Guo; Xiao-Long Wan; Xingang Zhang; Chang-Hua Ding; Xue-Long Hou

doi:10.1038/s41467-021-26667-0

Nature Communications (Nov 2021)

Regio- and enantioselective umpolung gem-difluoroallylation of hydrazones via palladium catalysis enabled by N-heterocyclic carbene ligand

Shuai Huang,
Fei-Fei Tong,
Da-Chang Bai,
Gao-Peng Zhang,
Yang-Jie Jiang,
Bo Zhang,
Xuebing Leng,
Ying-Long Guo,
Xiao-Long Wan,
Xingang Zhang,
Chang-Hua Ding,
Xue-Long Hou

Affiliations

Shuai Huang: State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS)
Fei-Fei Tong: Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, SIOC, CAS
Da-Chang Bai: State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS)
Gao-Peng Zhang: State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS)
Yang-Jie Jiang: State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS)
Bo Zhang: State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS)
Xuebing Leng: State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS)
Ying-Long Guo: State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS)
Xiao-Long Wan: Department of Analytic Chemistry, Center for Excellence in Molecular Synthesis, SIOC, CAS
Xingang Zhang: Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, SIOC, CAS
Chang-Hua Ding: Department of Chemistry, Innovative Drug Research Center, Shanghai University
Xue-Long Hou: State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry (SIOC), Chinese Academy of Sciences (CAS)

DOI: https://doi.org/10.1038/s41467-021-26667-0
Journal volume & issue: Vol. 12, no. 1
pp. 1 – 9

Abstract

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Installation of difluoroalkyl groups while also imparting stereochemical information is mostly only possible with organocatalytic methods that activate carbonyls. Here the authors show a method to perform an difluoroallylation of hydrazones, forming a masked amine stereocenter, via palladium- and N-heterocyclic-carbene catalysis.

Published in Nature Communications

ISSN: 2041-1723 (Online)
Publisher: Nature Portfolio
Country of publisher: United Kingdom
LCC subjects: Science
Website: https://www.nature.com/ncomms/

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