Photo‐Cross‐Coupling Reaction of Electron‐Rich Aryl Chlorides and Aryl Esters with Alkynes: A Metal‐Free Alkynylation | Zendy

Protti Stefano | Zendy; Fagi Maurizio | Zendy; Albini Angelo | Zendy

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Photo‐Cross‐Coupling Reaction of Electron‐Rich Aryl Chlorides and Aryl Esters with Alkynes: A Metal‐Free Alkynylation

Author(s) -

Protti Stefano,

Fagi Maurizio,

Albini Angelo

Publication year - 2005

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200501541

Subject(s) - aryl , sonogashira coupling , alkynylation , chemistry , halide , metal , coupling reaction , combinatorial chemistry , medicinal chemistry , palladium , photochemistry , organic chemistry , catalysis , alkyl

Photoheterolysis of aryl halides substituted with electron‐donating groups (EDGs) or aryl esters in 2,2,2‐trifluoroethanol (TFE) leads to phenyl cations, which can add to alkynes (see scheme, Tf=trifluoromethanesulfonyl). This reaction is an appealing metal‐free alternative to the (sila)‐Sonogashira reaction.

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