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8581376 
Journal Article 
Borane-Catalyzed Chemoselectivity-Controllable N-Alkylation and ortho C-Alkylation of Unprotected Arylamines Using Benzylic Alcohols 
Meng, SS; Tang, X; Luo, X; Wu, R; Zhao, JL; Chan, ASC 
2019 
ACS Catalysis
ISSN: 2155-5435 
American Chemical Society 
9 
9 
8397-8403 
English 
WOS:000485090400077 
An unprecedented protocol for the efficient and highly chemoselective alkylation of unprotected arylamines using alcohols catalyzed by B(C6F5)3 has been developed. The reaction gives N-alkylated products and ortho C-alkylated products in different solvents in good chemoselectivities and yields. Control experiments and DFT calculations indicated that the borane underwent alcohol/arylamine exchange to ensure catalytic activity, and a possible mechanism involving a carbocation is proposed. © 2019 American Chemical Society. 
B(C6F5)3; chemoselectivity-controllable; N-alkylation; ortho C-alkylation; unprotected arylamine