Development of the direct Suzuki-Miyaura cross-coupling of primary B-alkyl MIDA-boronates and aryl bromides

Jeffrey D St Denis; Conor C G Scully; C Frank Lee; Andrei K Yudin

doi:10.1021/ol500057a

Development of the direct Suzuki-Miyaura cross-coupling of primary B-alkyl MIDA-boronates and aryl bromides

Org Lett. 2014 Mar 7;16(5):1338-41. doi: 10.1021/ol500057a. Epub 2014 Feb 14.

Authors

Jeffrey D St Denis¹, Conor C G Scully, C Frank Lee, Andrei K Yudin

Affiliation

¹ Davenport Research Laboratories, Department of Chemistry, University of Toronto , 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.

PMID: 24527782
DOI: 10.1021/ol500057a

Abstract

The development of a palladium-catalyzed sp(3)-sp(2) Suzuki-Miyaura cross-coupling of B-alkyl-N-methyliminodiacetyl (B-alkyl MIDA) boronates and (hetero)aryl bromides is reported. This transformation is tolerant of a variety of functional groups (F, NO2, CN, Cl, COCH3, and CHO). B-Alkyl MIDA boronates allow an efficient cross-coupling reaction directed toward the synthesis of unsymmetrical methylene diaryls as well as alkylated arenes in good to excellent yields.