Rhodium(III)-Catalyzed C(sp)-H Functionalization of Cyclobutenes. Access to Cyclobuta[]pyridones and -pyridines.

Org Lett

Molecular, Macromolecular Chemistry, and Materials (C3M) , ESPCI Paris, CNRS (UMR7167), PSL University, 10 rue Vauquelin , Paris 75231 Cedex 05 , France.

Published: October 2019

-(ω-Alkynyl) hydroxamates derived from cyclobutenyl carboxylic acids were identified as viable substrates in intramolecular rhodium(III)-catalyzed heteroannulations, which led to diversely substituted cyclobuta[]pyridones. Further functionalization of the resulting cyclobutapyridones enabled the synthesis of cyclobuta[]pyridines and other nitrogen heterocycles after electrocyclic ring opening of the four-membered ring.

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http://dx.doi.org/10.1021/acs.orglett.9b03139DOI Listing

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