Ni-Catalyzed Remote Alcohol Substitution

C–C bond at remote site

Directly uses unprotected alkenyl alcohols with arylboronic acids to forge C–C bonds distal to the hydroxyl group, without preactivation, overcoming the usual β-H elimination preference.

Zhi-Kai, Zhang · Ji-Xuan, Zhang · Wang, Ming · Wu, Yichen · Yuan-Qing, Xu · Cao, Zhongyan · Wang, Peng

Journal of the American Chemical Society 2026

Advantages

No preactivation

Directly uses unprotected alkenyl alcohols, avoiding their conversion to halides or sulfonates, shortening the synthetic sequence.

Remote bond formation

Enables C–C bond formation at positions distal to the hydroxyl group, rather than at the original or allylic position.

Mild conditions

The reaction operates under mild and redox neutral conditions with good functional group compatibility.

Applications

• C–C bond formation methods：Forge C–C bonds at remote positions to expand accessible bond sites.
• Native alcohol functionalization：Directly functionalize native alcohols without preactivation.
• Arylboronic acid coupling：Couple arylboronic acids with alkenyl alcohols at remote sites for complex molecule synthesis.