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Regio-, diastereo- and enantioselectivity in the photocatalytic generation of carbanions via hydrogen atom transfer and reductive radical-polar crossover

Grotjahn, Sascha ; Müller, Lea ; Pattanaik, Aryaman ; Falk, Alexander ; Barison, Giorgia ; Bauer, Jonathan O. ; Rehbein, Julia ; Gschwind, Ruth M. ; König, Burkhard



Abstract

A sequence consisting of photocatalytic hydrogen atom abstraction (HAT), reductive radical‑polar crossover (RRPCO), and protonation/deuteration for stereochemical editing at benzylic positions is described. A systematic screening of substrates with benzylic C‑H bonds provides trends in reactivity for C‑H activation by silane thiols. A cis/trans isomerization of dihydrobenzofurans proceeding under ...

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