A radical hydroboration of electron-deficient alkenes was developed for the direct synthesis of diverse α-boryl functionalized molecules.

A regioselective radical hydroboration of gem-difluoroalkenes was developed for the synthesis of α-difluoroalkylborons. The reaction features excellent regioselectivity, broad substrate scope, and good functional group capability. DFT calculations implicated the remarkable α-selectivity was driven from the kinetically and thermodynamically more favorable α-addition step. The resulting α-difluoroalkylborons could be readily converted into NHC–borane-tethered monofluoroalkenes, which demonstrated unique reactivity and applicability in the synthesis of monofluoroalkene derivatives through transformations of the boron unit.

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A silyl radical-triggered radical addition-translocation-cyclization (RATC) process followed by chemo-divergent conversions was developed to construct structurally diverse silicon-incorporated indolines. The reaction proceeds via a sequence of silyl radical addition, 1,5-hydrogen...