Annulation of o-Quinodimethanes through N-Heterocyclic Carbene Catalysis for the Synthesis of 1-Isochromanones

Daniel Janssen-Müller; Santanu Singha; Theresa Olyschläger; Constantin G Daniliuc; Frank Glorius

doi:10.1021/acs.orglett.6b02335

Annulation of o-Quinodimethanes through N-Heterocyclic Carbene Catalysis for the Synthesis of 1-Isochromanones

Org Lett. 2016 Sep 2;18(17):4444-7. doi: 10.1021/acs.orglett.6b02335. Epub 2016 Aug 23.

Authors

Daniel Janssen-Müller¹, Santanu Singha¹, Theresa Olyschläger¹, Constantin G Daniliuc¹, Frank Glorius¹

Affiliation

¹ Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster , Corrensstraße 40, 48149 Münster, Germany.

PMID: 27549614
DOI: 10.1021/acs.orglett.6b02335

Abstract

The activation of 2-(bromomethyl)benzaldehydes using N-heterocyclic carbenes represents a novel approach to the generation of o-quinodimethane (o-QDM) intermediates. Coupling with ketones such as phenylglyoxylates, isatins, or trifluoromethyl ketones via [4 + 2] annulation gives access to functionalized 1-isochromanones.

Publication types

Research Support, Non-U.S. Gov't