Development and reactivity of novel benzo-fused phosphorus-containing heterocycles

Sabourin, Axel

Publication

Development and reactivity of novel benzo-fused phosphorus-containing heterocycles

Sabourin, Axel

Date

12/6/2021

Abstract

The work presented in this dissertation consists in the development of syntheses towards novel benzo-fused phosphorus-containing heterocycles. Special emphasis is given to benzophostam structures. A review of the most relevant literature in terms of preparation of known and related phosphorus-containing heterocycles is provided in Chapter I. The following chapter introduces a new concept invented by Montchamp and coworkers, the cost of academic methodologies (CAM), to evaluate and compare various methodologies according to a cost-based approach. The third chapter details the different strategies developed to synthesize the different P-substituted 5- and 6-membered benzophostams and they are evaluated through the CAM lense. Chapter IV is a direct continuation of chapter III with the development of methods to access various N- and C-substituted benzophostams by arylation or alkylation reactions with various electrophiles of phostams previously synthesized in chapter III or from completely new strategies, such as a reductive Heck approach. Finally, in chapter V, two new strategies are presented to access other type of P-heterocycles. The first one is based on the cyclization of unsaturated phosphorus compounds under Friedel-Crafts conditions to access electron rich benzo fused phosphorus-containing heterocycles while the second approach relies on [4+2] addition process of a benzooxaphosphole oxide with various permanent dipoles to deliver a series of 6-membered benzo-fused phosphorus-containing heterocycles.