An Improved Synthesis of Chiral 2,2′-Bipyridine Ligand C3-ACBP Without Column Chromatography

Zheng Liu; Sheng-Mei Lu; Bao-Qian Zhao; Hao-Dong Chen; Mu-Wang Chen; Yong-Gui Zhou

doi:10.1055/a-2063-1330

Synthesis, Table of Contents

Synthesis 2023; 55(16): 2483-2486
DOI: 10.1055/a-2063-1330

psp

Special Issue Honoring Prof. Guoqiang Lin’s Contributions to Organic Chemistry

An Improved Synthesis of Chiral 2,2′-Bipyridine Ligand C3-ACBP Without Column Chromatography

Zheng Liu

^aState Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P. R. of China

^bUniversity of Chinese Academy of Sciences, Beijing 100049, P. R. of China

,

Sheng-Mei Lu∗

^aState Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P. R. of China

,

Bao-Qian Zhao

^aState Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P. R. of China

,

Hao-Dong Chen

^aState Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P. R. of China

,

Mu-Wang Chen

^aState Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P. R. of China

,

Yong-Gui Zhou∗

^aState Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P. R. of China

› Author Affiliations

Abstract

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Abstract

A method for purifying compounds bearing pyridine structure from Mitsunobu reaction mixtures using zinc chloride and releasing bipyridines from Ullmann coupling reaction mixtures by using sulfide anion for competitively coordinating the copper ion were developed for the facile synthesis of the chiral 2,2′-bipyridine ligand (R_a ,S,S)-C3-ACBP. With these improvements, an improved synthesis of the chiral ligand at a 7 gram scale has been fulfilled in 48% overall yield without column chromatography within 3–4 days.

Key words

2,2′-bipyridine ligand - C3-ACBP - column chromatography free - zinc chloride - gram scale

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References

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