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Short Paper | Regular issue | Vol 94, No. 7, 2017, pp.1305-1313
Published online, 14th June, 2017
DOI: 10.3987/COM-17-13710
Selectivity of N- Versus O-Alkylation in Mitsunobu Reactions with Various Quinolinols and Isoquinolinols

Ryan E. Hartung,* Mark C. Wall, Sylvain Lebreton, Martin Smrcina, and Marcel Patek

*Icagen, 2090 E. Innovation Park Drive, Oro Valley, AZ 85755, USA

Abstract

Reacting quinolinols and isoquinolinols under Mitsunobu conditions can give rise to N-alkylated products in addition to the normally desired O-alkylated structures. An in-depth study of how the solvent, reagent equivalents, position of the quinoline/isoquinoline nitrogen and type of reacting aliphatic alcohol employed affect the ratio of N- versus O-alkylation is described.