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Chemoselective Homologation-Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes

Margherita Miele, Andrea Citarella, Thierry Langer, Ernst Urban, Martin Zehl, Wolfgang Holzer, Laura Ielo and Vittorio Pace*

*Department of Pharmaceutical Chemistry, University of Vienna, Althanstrasse, 14, 1090 Vienna, Austria, Email: vittorio.paceunivie.ac.at

M. Miele, A. Citarella, T. Langer, E. Urban, M. Zehl, W. Holzer, L. Ielo, V. Pace, Org. Lett., 2020, 22, 7629-7634.

DOI: 10.1021/acs.orglett.0c02831 (free Supporting Information)


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Abstract

A sequential installation of a carbenoid and a hydride into a carbonyl provides halomethyl alkyl derivatives with uniformly high yields and chemocontrol. The tactic is flexible and is not limited to carbenoids. Also, diverse carbanion-like species can act as nucleophiles.

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Dihalomethyl Homologation/Deoxygenation Sequence



Key Words

alkylation, deoxygenation, alkyl iodides, alkyl chlorides, silanes


ID: J54-Y2020