Journal
CHEMICAL COMMUNICATIONS
Volume 53, Issue 81, Pages 11185-11188Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7cc04397j
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- Princeton University
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The acid promoted addition of organotrifluoroborate salts to imine and enamine electrophiles is reported. Use of the pre-activated trifluoroboronate complex bypasses the need for alpha-hetero substitution on the electrophile component, greatly expanding the scope of the Petasis borono-Mannich reaction. A variety of vinyl, aromatic and heteroaromatic trifluoroborate salts undergo addition with good efficiency under mild reaction conditions. The reaction is amenable for use with a variety of carbamate protected imine and enamine electrophiles, achieving for the first time the effective coupling with aliphatic aldehydes.
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