Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 16, Pages 7308-7313Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01207
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Funding
- National Institute of General Medical Sciences [R01 GM 113878]
- National Science Foundation [CHE 1362841]
- Higher Education Commission (HEC), Pakistan [112-24510-2PS1-388]
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Iridium-and ruthenium-free approaches to protected allylic amines and alkyl nitriles under photoredox conditions are reported. An inexpensive organic dye, eosin Y, catalyzes coupling of Boc-protected potassium alpha-aminomethyltrifluoroborates with a variety of substituted alkenyl sulfones through an alpha-aminomethyl radical addition elimination pathway. Allylic and homoallylic amines were formed in moderate yields with high E/Z selectivity. The mechanistic approach was extended using tosyl cyanide as a radical trap, enabling the conversion of alkyltrifluoroborates to nitriles via a Fukuzumi acridinium-catalyzed process.
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