Premium
Cyclization of Diaryl(hetaryl)alkynes under Selenobromination Conditions: Regioselectivity and Mechanistic Studies
Author(s) -
Paegle Edgars,
Belyakov Sergey,
Petrova Marina,
Liepinsh Edvards,
Arsenyan Pavel
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500431
Subject(s) - regioselectivity , chemistry , alkene , electrophilic aromatic substitution , electrophile , electrophilic substitution , reagent , ring (chemistry) , organic chemistry , bromine , scavenger , combinatorial chemistry , inert gas , medicinal chemistry , radical , catalysis
The cyclization of substituted diaryl(hetaryl)alkynes with in‐situ‐prepared SeBr 4 has been achieved. The use of an alkene additive as a bromine scavenger gives simple access to functionalized benzo[ b ]selenophene and selenophenothiophene derivatives from commercially available or easily accessible starting materials. The reactions can be performed in air without the use of moisture‐sensitive reagents, dry solvents, or an inert atmosphere. Mechanistic studies confirmed a regioselective anti 1,2‐addition in the selenobromination step, and a subsequent electrophilic substitution in the aromatic ring to complete the cyclization.