Open AccessBrønsted Acid-Catalyzed Intramolecular Hydroarylation of β-Benzylstyrenes
Author(s) -
Xiao Cai,
Amir Keshavarz,
Justin D. Omaque,
Benjamin J. Stokes
Publication year - 2017
Publication title -
organic letters
Language(s) - Uncategorized
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.7b00958
Subject(s) - chemistry , geminal , steric effects , brønsted–lowry acid–base theory , intramolecular force , catalysis , boron , substrate (aquarium) , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , oceanography , geology
Using triphenylmethylium tetrakis(pentafluorophenyl)borate as a convenient Brønsted acid precatalyst, β-(α,α-dimethylbenzyl)styrenes are shown to cyclize efficiently to afford a variety of new indanes that possess a benzylic quaternary center. The geminal dimethyl-containing quaternary center is proposed to be necessary to arm the substrate for cyclization through steric biasing.