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可调节手性2,2'-联吡啶配体的设计与合成:在醛的对映选择性镍催化还原芳基化反应中的应用

Design and Synthesis of Tunable Chiral 2,2'-Bipyridine Ligands: Application to the Enantioselective Nickel-Catalyzed Reductive Arylation of Aldehydes.

作者信息

Zhang Shuai, Perveen Saima, Ouyang Yizhao, Xu Liang, Yu Tao, Zhao Min, Wang Linghua, Song Peidong, Li Pengfei

机构信息

Frontier Institute of Science and Technology, Xi'an Jiaotong University, Xi'an, Shaanxi 710054, China.

School of Chemistry, Xi'an Jiaotong University, Xi'an, Shaanxi 710049, China.

出版信息

Angew Chem Int Ed Engl. 2022 May 9;61(20):e202117843. doi: 10.1002/anie.202117843. Epub 2022 Feb 26.

DOI:10.1002/anie.202117843
PMID:35174597
Abstract

A new class of chiral 2,2'-bipyridine ligands, SBpy, featuring minimized short-range steric hindrance and structural tunability was rationally designed and developed, and the effectiveness was demonstrated in the first highly enantioselective Ni-catalyzed addition of aryl halides to aldehydes. In comparison with known approaches using preformed aryl metallic reagents, this reaction is more step-economical and functional group tolerant. The reaction mechanism and a model of stereocontrol were proposed based on experimental and computational results.

摘要

设计并开发了一类新型手性2,2'-联吡啶配体SBpy,其具有最小化的短程空间位阻和结构可调性,并在首例镍催化的芳基卤化物对醛的高度对映选择性加成反应中证明了其有效性。与使用预制芳基金属试剂的已知方法相比,该反应步骤经济性更高且对官能团耐受性更好。基于实验和计算结果提出了反应机理和立体控制模型。

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