Details

Autor(en) / Beteiligte

• Tian, Jun-Jie
• Zeng, Ning-Ning
• Liu, Ning
• Tu, Xian-Shuang
• Wang, Xiao-Chen

Titel

Intramolecular Cyclizations of Vinyl-Substituted N,N‑Dialkyl Arylamines Enabled by Borane-Assisted Hydride Transfer

Ist Teil von

• ACS catalysis, 2019-01, Vol.9 (1), p.295-300

Ort / Verlag

American Chemical Society

Erscheinungsjahr

2019

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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 α-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 sp3 carbon and an electron-rich olefin without using a transition metal or an external oxidant.