Rapid Room‐Temperature, Chemoselective C      sp     2     −C      sp     2      Coupling of Poly(pseudo)halogenated Arenes Enabled by Palladium(I) Catalysis in Air | Zendy

Kalvet Indrek | Zendy; Magnin Guillaume | Zendy; Schoenebeck Franziska | Zendy

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Rapid Room‐Temperature, Chemoselective C sp 2 −C sp 2 Coupling of Poly(pseudo)halogenated Arenes Enabled by Palladium(I) Catalysis in Air

Author(s) -

Kalvet Indrek,

Magnin Guillaume,

Schoenebeck Franziska

Publication year - 2017

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201609635

Subject(s) - catalysis , steric effects , chemistry , substrate (aquarium) , palladium , dimer , ligand (biochemistry) , coupling (piping) , photochemistry , coupling reaction , combinatorial chemistry , computational chemistry , organic chemistry , materials science , biochemistry , oceanography , receptor , metallurgy , geology

While chemoselectivities in Pd 0 ‐catalyzed coupling reactions are frequently non‐intuitive and a result of a complex interplay of ligand/catalyst, substrate, and reaction conditions, we herein report a general method based on Pd I that allows for an a priori predictable chemoselective Cs p2−Cs p2coupling at C−Br in preference to C−OTf and C−Cl bonds, regardless of the electronic or steric bias of the substrate. The C−C bond formations are extremely rapid (<5 min at RT) and are catalyzed by an air‐ and moisture‐stable Pd I dimer under open‐flask conditions.

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