We have studied the electrophilic fluorination of N-heterocyclic carbene (NHC) supported copper(I) vinyls. Alkynes can be directly converted to cis-(β-fluorovinyl)boronates in the presence of (NHC)copper(I) alkoxides and bis(neopentyl glycolato) diboron followed by addition of N-fluorobenzenesulfonimide (NFSI). Formation of a copper boryl and subsequent alkyne insertion into the Cu–B bond yields a copper(I) borovinyl that can be electrophilically quenched with NFSI to yield the corresponding cis-(β-fluorovinyl)boronate. The borofluorination of terminal alkynes provides access to α-fluorinated alkenes. The cis-(β-fluorovinyl)boronate esters are converted to potassium trifluoroborate salts and readily isolated. Further derivatization of the vinyl trifluoroborate generates a range of substituted fluorinated alkenes.

Carbon–fluorine bond formation from copper(I) vinyls: Synthesis of fluoroalkenes from alkynes

255th National Meeting (2018)

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