Iron-Catalyzed Electrophotochemical α‑Functionalization of a Silylcyclobutanol

Iron-Catalyzed Electrophotochemical α‑Functionalization of a Silylcyclobutanol

Four-membered ring structure is important in organic chemistry, and selective cleavage and functionalization of these strained rings are of great interest. However, direct α-functionalization of cyclobutanols is rarely reported because of the high O–H bond dissociation energy and the occurrence of β...

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Veröffentlicht in:Organic letters 2024-08, Vol.26 (34), p.7094-7099
Hauptverfasser: Zhou, Pan, Ding, Ling, Liu, Yuxiu, Song, Hongjian, Wang, Qingmin
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container_title Organic letters
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creator Zhou, Pan
Ding, Ling
Liu, Yuxiu
Song, Hongjian
Wang, Qingmin
description Four-membered ring structure is important in organic chemistry, and selective cleavage and functionalization of these strained rings are of great interest. However, direct α-functionalization of cyclobutanols is rarely reported because of the high O–H bond dissociation energy and the occurrence of β-scission of C–C bonds in these alcohols. Recently, transition-metal catalysis has facilitated alkoxy radical generation. Herein, we report a method for electrophotochemical α-functionalization of a silylcyclobutanol via visible-light-induced LMCT reactions of M-alkoxy complexes. Introduction of the silyl group into the cyclobutanol structure favored fast [1,2]-silyl transfer over ring opening, thus allowing the generation of α-functionalized products.
doi_str_mv 10.1021/acs.orglett.4c02279
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title Iron-Catalyzed Electrophotochemical α‑Functionalization of a Silylcyclobutanol
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