Nickel-Catalyzed One-Pot Deoxygenative Arylation of Benzylic Alcohols with Aryl Electrophiles Using TCT as an Activating Agent

Direct coupling of alcohols remains a challenge in current synthetic chemistry. We herein demonstrate a one-pot activation/coupling strategy for C(sp²)-C(sp³) cross-electrophile coupling of alcohols with aryl electrophiles using 2,4,6-trichloro-1,3,5-triazine as an activating agent. The reaction proceeds under mild conditions and tolerates various functionalities, including aldehyde, ketone, ester, lactone, nitrile, pyridine, quinoline, Ar-Bpin, and Ar-SiMe₃. Additionally, the electron-rich, electron-poor, and ortho-/meta-/para-substituted aryl electrophiles such as Ar-OTf, Ar-Br, and inert Ar-Cl all coupled well with benzyl alcohols. This one-pot protocol does not require preactivation of alcohols, thus providing a very robust and powerful alternative to the existing methods for the synthesis of diarylmethanes. The synthetic value of this operationally simple protocol was demonstrated by late-stage functionalization of complex molecules and gram-scale experiments.