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Bis(imino)pyridine Cobalt-Catalyzed Alkene Isomerization-Hydroboration: A Strategy for Remote Hydrofunctionalization with Terminal Selectivity

Jennifer V. Obligacion and Paul J. Chirik*

*Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States, Email: pchirikprinceton.edu

J. V. Obligacion, P. J. Chirik, J. Am. Chem. Soc., 2013, 135, 19107-19110.

DOI: 10.1021/ja4108148 (free Supporting Information)



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Abstract

A very active cobalt catalyst enables a facile anti-Markovnikov hydroboration of sterically hindered terminal alkenes. Notably, these hydroboration reactions proceed in neat substrates at 23C. With internal olefins, the cobalt catalyst provides a convenient method for hydrofunctionalization of remote C-H bonds by placing the boron substituent exclusively at the terminal positions of an alkyl chain.

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Key Words

alkyl boronates


ID: J48-Y2013