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One‐Pot Halogen Dance/Negishi Coupling of Dibromothiophenes for Regiocontrolled Synthesis of Multiply Arylated Thiophenes
Author(s) -
Okano Kentaro,
Sunahara Kazuhiro,
Yamane Yoshiki,
Hayashi Yuki,
Mori Atsunori
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604293
Subject(s) - negishi coupling , halogen , chemistry , dance , coupling (piping) , organic chemistry , combinatorial chemistry , materials science , art , catalysis , literature , alkyl , metallurgy
One‐pot halogen dance/Negishi cross‐coupling of readily available 2,5‐dibromothiophenes is described. A lithium diisopropylamide (LDA)‐mediated halogen dance reaction resulted in the formation of thermodynamically stable α‐lithiodibromothiophenes, which were transmetalated with ZnCl 2 and subjected to Negishi cross‐coupling to provide the corresponding arylated dibromothiophenes in one pot. The resultant β‐bromo group was much less reactive than the remaining α‐bromo group, which was used in a one‐pot double Suzuki–Miyaura cross‐coupling, enabling facile synthesis of multiply arylated thiophenes.