Intermolecular Enamine Mizoroki–Heck Reactions on a Bio-Derived Scaffold
Date
2024
Authors
Puschnig, J.
Jevric, M.
Sumby, C.J.
Greatrex, B.W.
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Journal of Organic Chemistry, 2024; 89(2):1315-1319
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Johannes Puschnig, Martyn Jevric, Christopher J. Sumby, and Ben W. Greatrex
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Abstract
The intramolecular enamine-Mizoroki−Heck reaction allows for the construction of nitrogen-containing heterocycles, although the related intermolecular version is less known. The reactions of enamines derived from Cyrene were investigated under Mizoroki−Heck conditions. An optimization study was used to identify that 1.5 mol % Pd(dba)2 with PC(y3) in xylene at reflux temperature gave the highest yield with electron-rich aryl iodides. Arylation occurred predominantly at the C−N center of the enamine, while the diastereoselectivity was dependent on the nitrogen substitution in the enamine.
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© 2024 American Chemical Society