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Robust Palladium‐Catalyzed Arylation of Catalyst‐Poisoning ortho ‐Sulfanyl Aryl Halides with Tetraarylborates and Its Application to Synthesis of π‐Extended Dibenzothiophenes
Author(s) -
Vasu Dhananjayan,
Hausmann Jan Niklas,
Saito Hayate,
Yanagi Tomoyuki,
Yorimitsu Hideki,
Osuka Atsuhiro
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700323
Subject(s) - chemistry , aryl , sulfanyl , halide , palladium , catalysis , iodide , combinatorial chemistry , organic chemistry , alkyl
Bis(tri‐ tert ‐butylphosphine)palladium‐catalyzed arylation of ortho ‐sulfanyl aryl halides with sodium tetraarylborates proceeds smoothly without any additional bases in high yields, providing a reliable route to 2‐sulfanylbiaryls. The conditions are applicable to aryl chloride and iodide as well as bromides. A variety of functional groups were tolerated. This arylation protocol offers a practical solution to overcome the poisoning behavior of aryl sulfides in such cross‐coupling arylation. In addition, our strategy provides a short and efficient access to dibenzothiophenes in combination with a Pummerer‐type cyclization.