Three Roles for the Fluoride Ion in Palladium‐Catalyzed Hiyama Reactions: Transmetalation of [ArPdFL 2 ] by Ar′Si(OR) 3 | Zendy

Amatore Christian | Zendy; Grimaud Laurence | Zendy; Le Duc Gaëtan | Zendy; Jutand Anny | Zendy

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Three Roles for the Fluoride Ion in Palladium‐Catalyzed Hiyama Reactions: Transmetalation of [ArPdFL 2 ] by Ar′Si(OR) 3

Author(s) -

Amatore Christian,

Grimaud Laurence,

Le Duc Gaëtan,

Jutand Anny

Publication year - 2014

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.201400956

Subject(s) - transmetalation , chemistry , fluoride , catalysis , reductive elimination , palladium , silicate , medicinal chemistry , ion , kinetic energy , inorganic chemistry , polymer chemistry , organic chemistry , physics , quantum mechanics

From the kinetic data on the transmetalation/reductive elimination in fluoride‐promoted Hiyama reactions, obtained using electrochemical techniques, it has been established that fluoride ions play three roles. F − reacts with trans ‐[ArPdBrL 2 ] (L=PPh 3 ) to form trans ‐[ArPdFL 2 ], which reacts with Ar′Si(OMe) 3 in the rate‐determining transmetalation, whereas trans ‐[ArPdBrL 2 ] does not react with Ar′Si(OMe) 3 . F − reacts with Ar′Si(OMe) 3 to deliver the unreactive silicate Ar′SiF(OMe) 3 − , thus leading to two antagonistic kinetic effects. In addition, F − catalyzes the reductive elimination from intermediate trans ‐[ArPdAr′L 2 ].

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