Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 8, Pages 5385-5394Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c00281
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Funding
- NSERC
- Canada Foundation for Innovation [17545, 19119]
- Province of Ontario
- Government of Ontario
- Ontario Graduate Scholarship (OGS)
- University of Toronto
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This paper describes a method for regioselective N-alkylation of various azole-type heterocycles using alkene or epoxide electrophiles. The activation of heterocyclic nucleophiles for selective N-functionalization is achieved by using diphenylborinic acid and an amine cocatalyst.
A method for regioselective N-alkylation of ambident, azole-type heterocycles with alkene or epoxide electrophiles is described. In the presence of diphenylborinic acid (Ph2BOH) andan amine cocatalyst, heterocyclic nucleophiles such as 1,2,3- and1,2,4-triazoles, substituted tetrazoles, and purine are activated towardselectiveN-functionalization. The scope of electrophilic partnersincludes enones, 2-vinylpyridine, phenyl vinyl sulfone, a dehydroala-nine derivative, and epoxides. Mechanistic studies, including in situ11B NMR spectroscopy and kinetic analysis, are discussed.
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