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Development of the Direct Suzuki–Miyaura Cross-Coupling of Primary B‑Alkyl MIDA-boronates and Aryl Bromides

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journal contribution
posted on 07.03.2014, 00:00 by Jeffrey D. St. Denis, Conor C. G. Scully, C. Frank Lee, Andrei K. Yudin
The development of a palladium-catalyzed sp3–sp2 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.