Carbonylation of Csp3 −H Bonds through Oxidative Wittig-Type Reaction: An Unprecedented Version of Wittig Reaction

The Wittig Reaction

The Wittig Reaction

This so-called Wittig reaction has a number of advantages over other olefination methods; in particular, it occurs with total positional selectivity (that is, an alkene always directly replaces a carbonyl group). By comparison, a number of other carbonyl olefination reactions often occur with double-bond rearrangement. In addition, the factors that influence Eand Z-stereoselectivity are well un...

Mechanism of the Phospha-Wittig–Horner Reaction**

General. All reactions were performed under argon using Schlenk techniques. Diethyl ether and THF were freshly distilled from sodium/benzophenone prior to use. 1 H, 13 C and 31 P spectra were recorded on a 400 MHz and 300 MHz spectrometers. Chemical shifts (ppm) were reported and referenced to the internal signal of residual protic solvent. High resolution mass spectral analyses (HRMS) were per...

Breaking the ring through a room temperature catalytic Wittig reaction.

One ring no longer rules them all: Employment of 2.5-10 mol % of 4-nitrobenzoic acid with phenylsilane led to the development of a room temperature catalytic Wittig reaction (see scheme). Moreover, these enhanced reduction conditions also facilitated the use of acyclic phosphine oxides as catalysts for the first time. A series of alkenes were produced in moderate to high yield and selectivity.

Using the Wittig reaction to produce alkenylcarbaboranes.

This communication reports the first use of the Wittig reaction to produce alkenylcarbaboranes.