Advanced Synthesis and Catalysis 2018-04-19

Iridium‐Catalyzed Tandem Cyclization of Benzoylacetonitriles with Diazo Compounds Leading to Substituted Naphtho[1,8‐bc]pyrans by Sequential C−H Functionalization

Kelu Yan; Bin Li; Baiquan Wang

Index: 10.1002/adsc.201800149

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Abstract

The cascade annulation reactions of benzoylacetonitriles with diazo compounds proceed efficiently in the presence of an iridium catalyst to give substituted naphtho[1,8‐bc]pyrans by sequential cleavage of C(sp2)−H/C(sp3)−H and C(sp2)−H/O−H bonds. Interestingly, the reactions involving cyclic diazo compounds and open‐chain diazo compounds lead to different types of naphtho[1,8‐bc]pyrans. Most products are obtained in moderate to good yields with a broad range of substrates.