Catalysis

Allylic rearrangement

Wolff rearrangement

Photochemistry

Alkylation

Biochemistry

Stereochemistry

Medicinal chemistry

Combinatorial chemistry

Organic chemistry

Sequence (biology)

Cycloaddition

Chemistry

Tsuji–Trost reaction

Ketene

Chemical Communications

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).

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