Regioselective Transition-Metal-Free Oxidative Cyclobutanol Ring Expansion to 4-Tetralones | Zendy

Philipp Natho | Zendy; Mia Kapun | Zendy; Lewis A. T. Allen | Zendy; Philip J. Parsons | Zendy

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Regioselective Transition-Metal-Free Oxidative Cyclobutanol Ring Expansion to 4-Tetralones

Author(s) -

Philipp Natho,

Mia Kapun,

Lewis A. T. Allen,

Philip J. Parsons

Publication year - 2018

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.8b03619

Subject(s) - tetralones , regioselectivity , chemistry , ring (chemistry) , acetonitrile , moiety , transition metal , oxidative phosphorylation , combinatorial chemistry , organic chemistry , catalysis , biochemistry

A facile and transition-metal-free ring expansion of the cyclobutanol moiety to 4-tetralones fused to heteroaromatic systems is described. The oxidative ring expansion proceeds rapidly and regioselectively through mediation by N-bromosuccinimide and acetonitrile in satisfactory to good yields. The preparation of precursors and the ring expansion have proven to be scalable and are straightforward to carry out.

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