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Regioselectivity Influences in Platinum-Catalyzed Intramolecular Alkyne O-H and N-H Additions

Jeff P. Costello and Eric M. Ferreira*

*Department of Chemistry, University of Georgia, Athens, Georgia 30602, United States, Email: emferruga.edu

J. P. Costello, E. M. Ferreira, Org. Lett., 2019, 21, 9934-9939.

DOI: 10.1021/acs.orglett.9b03557 (free Supporting Information)



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Abstract

The steric and electronic drivers of 5-exo and 6-endo regioselectivity in platinum-catalyzed intramolecular hydroalkoxylation are elucidated. The main influence arises from an electronic effect, where the alkyne substituent induces a polarization of the alkyne that leads to preferential heteroatom attack at the more electron-deficient carbon.


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Key Words

tetrahydrofurans


ID: J54-Y2019