Journal
ACS CATALYSIS
Volume 9, Issue 1, Pages 295-300Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b04485
Keywords
boron; hydride abstraction; cyclization; heterocycles; homogeneous catalysis
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Funding
- National Natural Science Foundation of China [21602114, 21871147]
- Natural Science Foundation of Tianjin [16JCYBJC42500]
- 1000-Talent Youth Program
- Fundamental Research Funds for Central Universities
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Catalytic amounts of B(C6F5)(3) have been found to be able to promote the intramolecular cyclization of vinyl-substituted N,N-dialkyl arylamines to afford nitrogen-containing heterocycles. Our mechanistic studies indicate the reaction is initiated by abstraction of an alpha-hydride from an N-alkyl substituent by B(C6F5)(3), which is followed by cyclization, and is concluded by delivery of the hydride to the cyclic cationic intermediate. The dual roles of B(C6F5)3, first as an oxidant and then as a hydride-carrying reductant, have enabled a rare redox-neutral cyclization process between a sp(3) carbon and an electron-rich oxidant. olefin without using a transition metal or an external oxidant.
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