# Stereospecific Coupling of Alcohols and Carbanion Nucleophiles through a Circular P(V) Activation Manifold

## TL;DR

A new method allows the efficient and safe formation of carbon-carbon bonds using alcohols and carbanion nucleophiles.

## Contribution

A redox-neutral, circular P(V) activation manifold enables stereospecific coupling without hazardous oxidants.

## Key findings

- Alkoxyphosphonium triflates are formed in situ and kinetically stable.
- Deoxyalkylation of alcohols occurs with inversion of configuration in moderate to excellent yields.

## Abstract

We report a method for the stereospecific construction
of sp3–sp3 carbon–carbon bonds
using alcohols
and carbanion nucleophiles. The process is based on a circular phosphorus­(V)
manifold which starts and ends with triphenylphosphine oxide. The
redox neutral approach eliminates the need for hazardous diazodicarboxylate
oxidants and allows for recovery and recycling of triphenylphosphine
oxide. Alcohol activation is achieved in situ through
formation of alkoxyphosphonium triflates, which are kinetically stable,
and undergo coupling with exogenous carbanion nucleophiles. In this
manner, a range of alcohols undergo deoxyalkylation with inversion
of configuration in moderate to excellent yield.