Robust Palladium‐Catalyzed Arylation of Catalyst‐Poisoning  ortho ‐Sulfanyl Aryl Halides with Tetraarylborates and Its Application to Synthesis of π‐Extended Dibenzothiophenes | Zendy

Vasu Dhananjayan | Zendy; Hausmann Jan Niklas | Zendy; Saito Hayate | Zendy; Yanagi Tomoyuki | Zendy; Yorimitsu Hideki | Zendy; Osuka Atsuhiro | Zendy

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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.

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