Ph3P/ICH2CH2I-promoted reductive deoxygenation of alcohols

Owing to the ubiquity of the hydroxyl group, reductive deoxygenation of alcohols has become an active research area. The classic Barton-McCombie reaction suffers from a tedious two-step procedure. New efficient methods have been developed, but they have some limitations, such as a narrow substrate scope and the use of moisture-sensitive Lewis acids. In this work, we describe the Ph3P/ICH2CH2I-promoted reductive deoxygenation of alcohols with NaBH4. The process is applicable to benzyl, allyl and propargyl alcohols, and also to primary and secondary alcohols, demonstrating a wide substrate scope and a good level of functional group tolerance. This protocol features convenient operation and low cost of all reagents.

Automated summary

Due to the widespread occurrence of hydroxyl groups, the reductive deoxygenation of alcohols is an active research area. This study presents a new efficient method using Ph3P/ICH2CH2I and NaBH4, which has a wide substrate scope, good functional group tolerance, and convenient operation with low reagent cost.