SET-Induced Biaryl Cross-Coupling: An SRN1 Reaction | Zendy

Brandon E. Haines | Zendy; Olaf Wiest | Zendy

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SET-Induced Biaryl Cross-Coupling: An S_RN1 Reaction

Author(s) -

Brandon E. Haines,

Olaf Wiest

Publication year - 2014

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo500222d

Subject(s) - set (abstract data type) , coupling (piping) , coupling reaction , chemistry , physics , mathematics , computer science , materials science , organic chemistry , composite material , catalysis , programming language

The SET-induced biaryl cross-coupling reaction is established as the first example of a Grignard S(RN)1 reaction. The reaction is examined within the mechanistic framework of dissociative electron transfer in the presence of a Lewis acid. DFT calculations show that the reaction proceeds through a radical intermediate in the form of an Mg ion-radical cage, which eludes detection in trapping experiments by reacting quickly to form an MgPh2 radical anion intermediate. A new mechanism is proposed.

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