cis‐Selective Transfer Semihydrogenation of Alkynes by Merging Visible‐Light Catalysis with Cobalt Catalysis,Advanced Synthesis & Catalysis

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cis‐Selective Transfer Semihydrogenation of Alkynes by Merging Visible‐Light Catalysis with Cobalt Catalysis
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-01-24 , DOI: 10.1002/adsc.201901562
Wan‐Fa Tian ₁ , Yong‐Qin He ₂ , Xian‐Rong Song ₁ , Hai‐Xin Ding ₁ , Jing Ye ₁ , Wen‐Jie Guo ₁ , Qiang Xiao ₁

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Herein, the first example of visible‐light‐driven, cobalt‐catalyzed transfer semihydrogenation of alkynes to alkenes is reported. It is carried out by using Ir[dF(CF₃)ppy]₂(dtbbpy)]PF₆ as photosensitizer, CoBr₂/n‐Bu₃P as proton‐reducing catalyst, and i‐Pr₂NEt/AcOH as the hydrogen source. Under the established catalytic system, the semihydrogenation proceeds with Z as the major selectivity and with inhibition of over‐reduction. Under mild reaction conditions, both internal and terminal alkynes, as well as reducible functional groups such as halogen, cyano, and ester, are tolerated. Preliminary mechanistic studies revealed the dual role of the photosensitizer in initiating the reaction via a single‐electron transfer process and controlling the stereoselectivity via an energy transfer process.

中文翻译：

可见光催化与钴催化相结合的炔烃顺式选择性转移半氢化反应

本文报道了第一个可见光驱动，钴催化的炔烃转移半氢化成烯烃的例子。通过使用Ir [dF（CF ₃）ppy] ₂（dtbbpy）] PF ₆作为光敏剂，CoBr ₂ / n- Bu ₃ P作为质子还原催化剂，以及i- Pr ₂ NEt / AcOH作为氢来进行资源。在已建立的催化体系下，半氢化与Z一起进行作为主要的选择性，并抑制过度还原。在温和的反应条件下，内部和末端炔烃以及可还原的官能团（如卤素，氰基和酯）均可以耐受。初步的机理研究表明，光敏剂在通过单电子转移过程引发反应和通过能量转移过程控制立体选择性方面起着双重作用。

更新日期：2020-01-24

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