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Org Lett. 2018 Oct 19;20(20):6530-6533. doi: 10.1021/acs.orglett.8b02856. Epub 2018 Oct 9.

Palladium(II)-Catalyzed C(sp2)-H Carbonylation of Sterically Hindered Amines with Carbon Monoxide.

Author information

1
Hefei National Laboratory for Physical Sciences at the Microscale and Department of Chemistry, Center for Excellence in Molecular Synthesis of CAS , University of Science and Technology of China , 96 Jinzhai Road , Hefei 230026 , China.
2
College of Chemistry, Chemical Engineering and Material Science, Collaborative Innovation Center of Functionalized Probes for Chemical Imaging in Universities of Shandong, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Institute of Molecular and Nano Science , Shandong Normal University , Jinan 250014 , China.

Abstract

A palladium-catalyzed, amine-directed C(sp2)-H carbonylation of α,α-disubstituted benzylamine under 1 atm of CO for the facile synthesis of sterically hindered benzolactam has been developed. The key to success is the use of 2,2,6,6-tetramethyl-1-piperidinyloxy as the crucial sole oxidant. The synthetic utility of this transformation has been demonstrated by the first concise synthesis of the natural product spiropachysin-20-one.

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