Visible Light Promoted Brominative Dearomatization of Biaryl Ynones to Spirocycles.

J Org Chem

Organic Synthesis and Molecular Engineering Laboratory, Department of Chemistry, Indian Institute of Technology Indore, Indore, Madhya Pradesh 453552, India.

Published: August 2023

Bromine induced spiro cyclization of biaryl ynones facilitated the synthesis of spiro[5,5]trienones suitable for extended functionality at the C(3') position. Herein, a step-economic photo-oxidative brominative carbannulation of biaryl ynones employing ammonium bromide and riboflavin tetraacetate (RFTA) has been developed. The reactivity between distal phenyl C-H activated -annulation and dearomative -annulation is well exemplified. The eminent features of the methodology include metal-free, external additive free, low-loading photocatalyst (0.1 mol %), and use of a simple precursor.

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http://dx.doi.org/10.1021/acs.joc.3c00941DOI Listing

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