Premium
Visible‐Light‐Enabled Stereodivergent Synthesis of E ‐ and Z ‐Configured 1,4‐Dienes by Photoredox/Nickel Dual Catalysis
Author(s) -
Song Fan,
Wang Fang,
Guo Lei,
Feng Xiaoliang,
Zhang Yanyan,
Chu Lingling
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201909543
Subject(s) - stereoselectivity , allylic rearrangement , catalysis , electrophile , chemistry , photoredox catalysis , alkene , nickel , photocatalysis , combinatorial chemistry , coupling reaction , photochemistry , organic chemistry
A stereodivergent reductive coupling reaction between allylic carbonates and vinyl triflates to furnish both E ‐ and Z ‐configured 1,4‐dienes has been achieved by visible‐light‐induced photoredox/nickel dual catalysis. The mild reaction conditions allow good compatibility of both vinyl triflates and allylic carbonates. Notably, the stereoselectivity of this synergistic cross‐electrophile coupling can be tuned by an appropriate photocatalyst with a suitable triplet‐state energy, providing a practical and stereodivergent means to alkene synthesis. Preliminary mechanistic studies shed some light on the coupling step as well as the control of the stereoselectivity step.