4.5 Review

Stereoselective Hydrogen Atom Transfer in Free Radical Reactions

Journal

ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 12, Issue 6, Pages -

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202300175

Keywords

C-H functionalization; Hydrogen Atom Transfer; Lewis acid catalysis; photoenzymatic catalysis; Polarity Reversal catalysis

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Hydrogen atom transfer (HAT) is an important class of radical reactions. Despite extensive research, controlling the stereoselectivity of the HAT process remains challenging. This review highlights the use of small molecule chiral HAT reagents and catalysts to achieve stereoselectivity in free radical reactions, as well as the recent advancements in photoenzymatic catalysis for efficient HAT reactions.
Hydrogen atom transfer (HAT) is one of the important class of radical reactions. Although extensive research into this elementary step has resulted in the discovery of many compounds capable of functioning as HAT reagents, synthetic methods available to control the stereoselectivity of the HAT process remains challenging. This mini review outlines how small molecule chiral HAT reagents and catalysts were used to achieve stereoselectivity (diastereoselectivity and enantioselectivity) in free radical reactions. The review also focuses on the recent surge in photoenzymatic catalysis to achieve efficient HAT reactions.

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