Pd-Catalyzed coupling of benzyl bromides with BMIDA-substituted N -tosylhydrazones: synthesis of trans -alkenyl MIDA boronates

A palladium-catalyzed stereoselective synthesis of alkenyl boronates from -methyliminodiacetyl boronate (BMIDA)-substituted -tosylhydrazone and benzyl bromides is developed. A range of -alkenyl MIDA boronates as single stereoisomers were obtained in moderate yields with good functional group compati...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2022-01, Vol.58 (3), p.399-402
Main Authors: Li, Shichao, Li, Muyao, Li, Shu-Sen, Wang, Jianbo
Format: Article
Language:English
Subjects:
Bromides
Chemical reactions
Chemical synthesis
Coupling (molecular)
Cross coupling
Functional groups
Palladium
Stereoisomerism
Stereoselectivity
Substitutes
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Summary:A palladium-catalyzed stereoselective synthesis of alkenyl boronates from -methyliminodiacetyl boronate (BMIDA)-substituted -tosylhydrazone and benzyl bromides is developed. A range of -alkenyl MIDA boronates as single stereoisomers were obtained in moderate yields with good functional group compatibility. The resultant boronate products may be transformed to other boron-containing compounds and may also be directly used in cross-coupling reactions.
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc06170d