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Synthesis of Highly Functionalized 12-Membered Trifluoromethyl Heterocycles via a Nondecarboxylative Pd-Catalyzed [6 + 6] Annulation
An efficient method for the construction of 12-membered heterocycles with a trifluoromethyl group (3) was achieved via a nondecarboxylative Pd-catalyzed [6 + 6] annulation of six-membered trifluoromethyl benzo[d][1,3]oxazinones (1) with four-membered vinyl oxetanes (2). A variety of relatively la...
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Published in: | ACS catalysis 2020-01, Vol.10 (2), p.1454-1459 |
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Main Authors: | , , , |
Format: | Article |
Language: | English |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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Summary: | An efficient method for the construction of 12-membered heterocycles with a trifluoromethyl group (3) was achieved via a nondecarboxylative Pd-catalyzed [6 + 6] annulation of six-membered trifluoromethyl benzo[d][1,3]oxazinones (1) with four-membered vinyl oxetanes (2). A variety of relatively large heterocycles 3 featuring a stereogenic trifluoromethylated carbon center, an amino group, as well as an alkenyl and a carbonate moiety were obtained. An X-ray crystallographic analysis revealed a unique 3D architecture of the products that affords an attractive chemical space. Whereas the method can be applicable for nonfluorinated substrates, the trifluoromethyl group plays a vital role in this unexpected Pd-catalyzed nondecarboxylative ring expansion. |
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ISSN: | 2155-5435 2155-5435 |
DOI: | 10.1021/acscatal.9b05377 |