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Published on: April 2, 2018
Oxidative Cleavage of β-Substituted Primary Alcohols in Flow
Michael Tapera1, Athanasios Savvidis1, Cedric Meysing1
1Organic Chemistry, Bergische Universität Wuppertal, Gaußstr. 20, 42119, Wuppertal, Germany.
None:
Herein, we report a scalable oxidative cleavage of β-substituted primary alcohols under continuous-flow conditions using a silica-supported hypervalent iodine(V) catalyst and TBA-Oxone as terminal oxidant. The method enables rapid and selective synthesis of γ-lactones and γ-lactams under mild conditions with broad substrate scope and high functional group tolerance. The catalyst is reusable for >15 cycles, and the process is readily scalable. Moreover, this technology offers a readily scalable and sustainable process for the synthesis of γ-butyrolactone from tetrahydrofurfuryl alcohol.
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