Silver triflate catalyzed cyclopropyl carbinol rearrangement for benzo[b]oxepine and 2H-chromene synthesis
Chan, Philip Wai Hong
Teo, Wan Teng
Koh, Shaun Wei Yong
Lee, Bo Ra
Ayers, Benjamin James
Date of Issue2015
School of Physical and Mathematical Sciences
An efficient AgOTf-catalyzed (TfO = trifluoromethanesulfonate) cyclopropyl carbinol rearrangement for the synthesis of benzo[b]oxepines and 2H-chromenes is reported by starting from 2-[cyclopropyl(hydroxy)methyl]phenols. The reactions proved to be general in scope and furnished a range of the corresponding functionalized oxygen heterocycles. The formation of the benzo-fused six-membered adduct is proposed to result from the ring-contraction of the benzo[b]oxepine derivative. Control of the product selectivity is achievable by fine-tuning the reaction time. The catalytic synergy between the silver(I) cation and the triflate anion was essential for optimal product yields.
DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis
European journal of organic chemistry
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