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A photoinduced Wolff rearrangement/Pd-catalyzed [3+2] cycloaddition sequence: an unexpected route to tetrahydrofurans

Author:
Liu, Jie, Li, Miao-Miao, Qu, Bao-Le, Lu, Liang-Qiu, Xiao, Wen-Jing
Source:
Chemical communications 2019 v.55 no.14 pp. 2031-2034
ISSN:
1364-548X
Subject:
alkylation, catalytic activity, chemical communication, cycloaddition reactions, palladium, tetrahydrofuran
Abstract:
A novel sequential reaction that combines a visible light-induced Wolff rearrangement of α-diazoketones and a Pd-catalyzed [3+2] cycloaddition of vinyl cyclopropanes with the resulting ketenes is described in this work. Selective O-allylic alkylation was observed over C-allylic alkylation, which unexpectedly led to a series of highly functionalized tetrahydrofurans with high efficiency (20 examples, 58–99% yields).
Agid:
6308055