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Copper-Catalyzed Stereospecific Transformations of Alkylboronic Esters
Ningxin Xu1, Hao Liang1, James P Morken1
1Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, United States.
Abstract:
Copper-catalyzed stereospecific cross-couplings of boronic esters are reported. Boron "ate" complexes derived from pinacol boronic esters and tert-butyl lithium undergo stereospecific transmetalation to copper cyanide, followed by coupling with alkynyl bromides, allyl halides, propargylic halides, β-haloenones, hydroxylamine esters, and acyl chlorides. Through this simple transformation, commercially available inexpensive compounds can be employed to convert primary and secondary alkylboronic esters to a wide array of synthetically useful compounds.
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