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

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 a...

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Published inOrganic letters Vol. 16; no. 5; pp. 1338 - 1341
Main Authors St. Denis, Jeffrey D, Scully, Conor C. G, Lee, C. Frank, Yudin, Andrei K
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.03.2014
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ELECTROPHILIC DISPLACEMENT REACTIONS
BORONIC ACIDS
HYDROBORATION
MECHANISM
PROTODEBORONATION
RETENTION
ARENES
OXIDATIVE-ADDITION
PALLADIUM COMPLEX
LIGAND
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Summary: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.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol500057a