Highly efficient 1,4-additions of electron-deficient aryl boronic acids

ORGN 681

William C. Trenkle, trenkle@Brown.edu, Julia L. Barkin, Marcus D. Faust Jr., and Dwight A. Sweigart, Dwight_Sweigart@Brown.edu. Department of Chemistry, Brown University, Box H, Providence, RI 02912
The conjugate addition of aryl boronic acids to unsaturated carbonyl compounds is a versatile and mild approach to carbon-carbon bond formation. We report the application of a new rhodium quinone catalyst that provides a mild, highly effective and operationally facile procedure for conjugate addition of aryl boronic acids to conjugate acceptors. Our method is effective for a wide range of electron rich and deficient aryl boronic acids requiring low catalyst loading (0.5 mol%) and low boronic acid equivalency (1.2 equiv. relative to olefin) affording excellent yields (91-99%) of addition adducts.