Journal
ACS CATALYSIS
Volume 4, Issue 5, Pages 1564-1569Publisher
AMER CHEMICAL SOC
DOI: 10.1021/cs500130y
Keywords
hydroboration; carboboration; copper; alkynes; N-heterocyclic carbenes
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Funding
- Royal Society (University Research Fellowship)
- EaStCHEM School of Chemistry
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The first in air copper-catalyzed method for the selective synthesis of tri- and tetrasubstituted vinylboronate derivatives is presented. Three different variants of the borylation of internal alkynes (alpha-hydroboration, beta-hydroboration, and carboboration) are described using a single catalyst: [Cu(Cl)(IMes)] (IMes = N,N'-bis-[2,4,6-(trimethyl)phenyl]-imidazol-2-ylidene) without taking any precaution to avoid the presence of air. Bis(pinacolato)diboron was used to afford beta-hydroborated products in the presence of methanol. Adding instead another electrophile allowed the formation of tetrasubstituted vinylboronate species. Finally, the alpha-products were obtained using pinacolborane as the boron source. All compounds were obtained in high yield with excellent regioselectivity at low catalyst loading (0.04-2, mol %). The protocol constitutes a very convenient route to access these highly valuable molecules.
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