Journal
ACS CATALYSIS
Volume 8, Issue 4, Pages 3673-3677Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b00074
Keywords
thorium; dearomatization; pyridine; N-heteroaromatic; 1,2-regioselective
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Funding
- Israel Science Foundation [78/14]
- PAZY Foundation Fund
- Technion-Guangdong Fellowship Program
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The thorium methyl and hydride complex (C5Me5)(2)ThMe2 and [(C5Me5)(2)Th(H)(mu-H)](2) catalyzed highly 1,2-regioselective dearomatization of pyridines via a hydroboration process is reported herein. Twelve different kinds of meta- and para-substituted pyridines are applicable to this reaction, giving the corresponding N-bory1-1,2-dihydropyridine products in high yields. Other N-heteroaromatic compounds, such as benzo-fused N-heterocycles, pyrazines, pyrimidines, 1,3,5-triazine, and benzothiazole, were also found to be hydroborated with high chemoselectivity. Kinetics including isotope effect studies revealed a first-order dependence on the concentration of catalyst, pyridine, and pinacolborane, with release of the dearomatized final product as the rate-determining step. A plausible mechanism is proposed on the basis of stoichiometric reactions and kinetic studies.
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