Synthesis 2017; 49(03): 579-586
DOI: 10.1055/s-0036-1588884
paper
© Georg Thieme Verlag Stuttgart · New York

Hydroarylation of (E)-5-(2-Arylethenyl)-2-methyl-2H-tetrazoles under Superelectrophilic Activation

Anna D. Lisakova
a   Saint Petersburg State Institute of Technology (Technical University), Moskovsky pr., 26, Saint Petersburg, 190013, Russian Federation
,
Dmitry S. Ryabukhin
b   Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, 199034, Russian Federation
c   Department of Chemistry, Saint Petersburg State Forest Technical University, Institutsky per., 5, Saint Petersburg, 194021, Russian Federation   Email: rost_trifonov@mail.ru   Email: aleksvasil@mail.ru   Email: a.vasilyev@spbu.ru
,
Rostislav E. Trifonov*
a   Saint Petersburg State Institute of Technology (Technical University), Moskovsky pr., 26, Saint Petersburg, 190013, Russian Federation
b   Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, 199034, Russian Federation
,
Vladimir A. Ostrovskii
a   Saint Petersburg State Institute of Technology (Technical University), Moskovsky pr., 26, Saint Petersburg, 190013, Russian Federation
,
Irina A. Boyarskaya
b   Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, 199034, Russian Federation
,
Aleksander V. Vasilyev*
b   Institute of Chemistry, Saint Petersburg State University, Universitetskaya nab., 7/9, Saint Petersburg, 199034, Russian Federation
c   Department of Chemistry, Saint Petersburg State Forest Technical University, Institutsky per., 5, Saint Petersburg, 194021, Russian Federation   Email: rost_trifonov@mail.ru   Email: aleksvasil@mail.ru   Email: a.vasilyev@spbu.ru
› Author Affiliations
Further Information

Publication History

Received: 23 August 2016

Accepted after revision: 29 August 2016

Publication Date:
21 September 2016 (online)


Abstract

The reaction of 5-(2-arylethenyl)-2-methyl-2H-tetrazoles with arenes (benzene, xylenes, tert-butylbenzene, anisole, veratrole, 1,2-dichlorobenzene) under conditions of superelectrophilic activation under the action of Brønsted superacids (CF3SO3H, FSO3H) or strong Lewis acids (AlCl3, AlBr3) leads regioselectively to the products of hydroarylation of the carbon–carbon double bond, viz., 5-(2,2-diarylethenyl)-2-methyl-2H-tetazoles, in yields of up to 95%.

Supporting Information

 
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