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Suzuki Cross‐Couplings of Alkyl Tosylates that Possess β Hydrogen Atoms: Synthetic and Mechanistic Studies
Author(s) -
Netherton Matthew R.,
Fu Gregory C.
Publication year - 2002
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 - 10.1002/1521-3773(20021018)41:20<3910::aid-anie3910>3.0.co;2-w
Subject(s) - alkyl , chemistry , hydrogen , combinatorial chemistry , computational chemistry , stereochemistry , organic chemistry
A striking dependence of reactivity on phosphane structure was observed in the first Suzuki‐type cross‐coupling process that is effective for functionalized alkyl tosylates. In this reaction, in which solely commercially available reagents are used, P t Bu 2 Me is the ligand of choice. Through the use of deuterium‐labeled compounds, it has been established that the coupling proceeds with predominant inversion of configuration at the carbon atom [Eq. (1), 9‐BBN=9‐borabicyclo[3.3.1]nonane].