Benzocyclobutenone Synthesis Exploiting Acylsilanes As Photofunctional Directing Groups

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2024 Nov 6

PMID 39502503

Authors

Rowan L Pilkington

Hannah J Ross

Liselle Atkin

Daniel L Priebbenow

Affiliations

Soon will be listed here.

Abstract

The visible-light irradiation of acylsilane tethered vinyl ketones promotes an intramolecular Stetter-type reaction siloxycarbene intermediates. To exploit this unique mode of reactivity, we herein describe the innovative use of acylsilanes as photofunctional directing groups. First, an acylsilane directed ruthenium catalysed C-H olefination reaction was developed to generate benzoylsilanes bearing vinyl ketone functionality. Then, visible-light irradiation initiated the 1,4-conjugate addition of transient siloxycarbene intermediates with pendent vinyl ketones to afford unique benzocyclobutenone scaffolds primed for further synthetic elaboration.

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