Brønsted Acid-Catalyzed Intramolecular Hydroarylation of β-Benzylstyrenes | Zendy

Xiao Cai | Zendy; Amir Keshavarz | Zendy; Justin D. Omaque | Zendy; Benjamin J. Stokes | Zendy

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Brønsted 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 , 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.

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