Rh(III)-Catalyzed C–H Activation of Benzoylacetonitriles and Tandem Cyclization with Diazo Compounds to Substituted Benzo[de]chromenes

• DOI: 10.1021/acs.orglett.8b00103
• Publication Date: 2018-03-22T19:08:06Z
• Authors: Feifei Fang; Chunmei Zhang; Chaofan Zhou; Yazhou Li; Yu Zhou; Hong Liu
• Keywords: 01 natural sciences; 0104 chemical sciences

Rh (III)-catalyzed C-H activation of benzoylacetonitriles in coupling with diazo compounds was developed to synthesize diversified substituted benzo[ de]chromenes via a formal (4 + 2) cycloaddition with a diazo compound and subsequent tandem (4 + 2) cycloaddition with another diazo compound. Intriguingly, synthesis of substituted benzo[ de]chromenes and their decarboxylation products could be realized by controlling the reaction conditions. These reactions have a broad range of substrates, moderate to good yields, and high regioselectivity.