Environmentally friendly Miyaura Borylations allowing for green, 1-pot borylation/Suzuki-Miyaura couplings

Current routes to boronic acids and their corresponding esters to be used in subsequent Suzuki-Miyaura (SM) cross couplings impact the cost, waste, and safety concerns associated with generating these materials. A new method for installing the ethyl pinacol boronic ester, or B(Epin) derivative leads...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2024-09, Vol.26 (19), p.1115-1122
Main Authors: Nelson, Chandler B, L'Heureux, Scott J, Wong, Madison J, Kuhn, Simone L, Ghiglietti, Erika, Lipshutz, Bruce H
Format: Article
Language:English
Subjects:
Chemical reactions
Couplings
Esters
Palladium
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Summary:Current routes to boronic acids and their corresponding esters to be used in subsequent Suzuki-Miyaura (SM) cross couplings impact the cost, waste, and safety concerns associated with generating these materials. A new method for installing the ethyl pinacol boronic ester, or B(Epin) derivative leads to stable borylated products under near-neat conditions using high concentrations of a green solvent and moderate reaction temperatures, catalyzed by relatively low palladium loadings. Alternatively, the newly fashioned Ar-B(Epin) can be generated in situ and used directly in the same pot for SM reactions leading to aromatic and heteroaromatic residues characteristic of the biaryl products being formed. An array of complex targets, including API-related products, can be generated via this green and environmentally responsible methodology. A new method for installing the B(Epin) boronic ester leads to stable, functionalized borylated aromatic products under near-neat conditions, thereby allowing for sustainable Suzuki-Miyaura couplings.
ISSN:1463-9262
1463-9270
DOI:10.1039/d4gc03115f