Nickel(ii)-catalyzed highly selective 1,2-diborylation of non-activated monosubstituted alkenes

Abstract

A practical method for 1,2-diborylation of non-activated monosubstituted alkenes via nickel catalysis has been developed. The protocol features with high functional group tolerance and can be applied for the formal...

Selective Fluorosulfonylation of Thianthrenium Salts Enabled by Electrochemistry

“…Although these protocols show excellent applications, they mainly rely on the use of transition metal catalysis or photoredox catalysis to activate thianthrenium salts (Figure B). − Broadening the synthetic applicability with the new activation model remains underdeveloped . In this context, considering that the reductive potential of stable and easy-to-handle aryl thianthrenium salts (TT) is around −1.5 V (vs SCE) and driven by the intrinsic advantage of electrosynthesis using electron as a green redox reagent to activate substrates under mild reaction conditions, we envisioned that thianthrenium salts should be facilely reduced to form the carbon-based radicals at the cathode under a suitable voltage, based on our previous works . Such an electrochemical activation strategy might afford new advances in thianthrenium salt chemistry, and the tunable redox ability of the electrochemical strategy should be able to reduce both aryl and alkyl thianthrenium salts, to form the corresponding aryl and nonstabilized alkyl radicals, respectively.…”

A general nickel-catalyzed highly regioselective hydroarylation of unactivated alkenes enabled by the picolinamide auxiliary

“…11 d However, the substrate scope was only limited to monosubstituted aliphatic alkenes. Herein, with our continuing interest in nickel chemistry 14 and alkene difunctionalization, 15 we wish to report our recent discovery that the employment of simple nickel catalysis without an external ligand enables us to efficiently realize the designed hydroarylation of both γ- or δ-vinyl amides with excellent regioselectivity and broad functional group tolerance (Scheme 1D). Noticeably, a series of non-activated mono-, di- and trisubstituted alkenes that have not been well-developed in previous hydroarylation reactions 10–13 all worked smoothly with excellent regioselectivity in our hands.…”