Visible light-promoted reactions with diazo compounds: a mild and practical strategy towards free carbene intermediates

Chemical Society Reviews
Zhen YangRene M Koenigs

Abstract

Carbenes are important intermediates in organic chemistry and have been widely applied in various types of organic reactions, ranging from cycloaddition reactions and sigmatropic rearrangements to C-H functionalizations, thus allowing the rapid construction of densely functionalized molecules. Over the past decades, remarkable progress has been achieved in metal-catalyzed carbene transfer reactions. Nevertheless, realizing these transformations under milder and/or greener conditions is still highly desirable. Only recently, visible light-promoted carbene transfer reactions of diazo compounds via free carbene intermediates have emerged as a practical, mild and powerful tool. In this tutorial review, we summarize the latest advances in the area, aiming at providing a clear overview on reaction design, mechanistic scenarios and potential future developments.

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Citations

Dec 17, 2020·Organic & Biomolecular Chemistry·Jingya YangCongde Huo
Feb 4, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·David P DayAntonio C B Burtoloso
Mar 18, 2021·Organic Letters·Daniel L PriebbenowAnastasios Polyzos
Apr 7, 2021·The Journal of Organic Chemistry·Pietro CapurroAndrea Basso
Apr 19, 2021·The Journal of Organic Chemistry·Shuai ZhaoXin Chen
May 29, 2021·Chemical Communications : Chem Comm·Sourav Sekhar BeraRene M Koenigs

Methods Mentioned

BETA
column chromatography

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