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Palladium‐Catalyzed Suzuki–Miyaura Reaction Involving a Secondary sp 3 Carbon: Studies of Stereochemistry and Scope of the Reaction
Author(s) -
Rodríguez Nuria,
Ramírez de Arellano Carmen,
Asensio Gregorio,
MedioSimón Mercedes
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200601488
Subject(s) - stereospecificity , stereocenter , chemistry , palladium , reagent , catalysis , coupling reaction , medicinal chemistry , substrate (aquarium) , hydride , carbon–carbon bond , enantioselective synthesis , combinatorial chemistry , organic chemistry , metal , oceanography , geology
Palladium‐catalyzed CC bond formation involving secondary sp 3 ‐hybridized carbon is described. These reactions occur with secondary 1‐bromoethyl arylsulfoxides and different arylboronic acids, to produce the corresponding arylated sulfoxides in moderate to high yields and with complete stereospecificity. Despite the presence of β hydrogens in the substrate, the competitive β‐hydride elimination is not a significant side reaction when coordinating solvents are used. The reported cross‐coupling involves secondary C sp 3C sp 2bond formation: this is the first time that a mechanistic study has been carried out with such substrates. The reaction proceeds with inversion of configuration at the stereogenic C sp 3carbon. The high stereospecificity of the coupling and the mildness of the reaction conditions allow for the preservation of the optical purities of reagents and products and the preparation of useful chiral targets.