A New Use of Wittig-Type Reagents as 1,3-Dipolar Cycloaddition Precursors and in Pyrrole Synthesis

2007/09/20 by Daniel J. St‐Cyr, Bruce A. Arndtsen · 8 citations
Chemistry · #Phosphorus compounds and reactions #Synthesis and Characterization of Pyrroles #Synthesis and Reactivity of Heterocycles

paper · doi:10.1021/ja074330w

openalex publication_date 2007/09/20 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/26

Abstract

The one-pot reaction of imines, acid chlorides, and phosphonites has been found to generate a new class of phosphorus-based 1,3-dipolar cycloaddition reagent. These substrates, which are isomeric forms of classic Wittig reagents, undergo cycloaddition reactions in an analogous fashion to 1,3-oxazolium-5-oxides (Münchnones). However, these 1,3-dipoles can be generated in one pot, in a modular fashion, and directly from available reagents, suggesting their potential general utility in heterocycle synthesis. The latter is illustrated in the design of a phosphonite-mediated synthesis of pyrroles from a variety of imines, acid chlorides, and alkynes.

Cited by

• Metal-Free, Multicomponent Synthesis of Pyrrole-Based π-Conjugated Polymers from Imines, Acid Chlorides, and Alkynes
• Münchnones—New Facets after 50 Years
• Cyclic 1,3-Dipoles or Acyclic Phosphonium Ylides? Electronic Characterization of “Montréalones”
• Multicomponent Synthesis of Substituted and Fused-Ring Imidazoles via Phospha-münchnone Cycloaddition
• Modular Mesoionics: Understanding and Controlling Regioselectivity in 1,3-Dipolar Cycloadditions of Münchnone Derivatives
• Phospha-Münchnones: Electronic Structures and 1,3-Dipolar Cycloadditions
• Chiral Phosphorus-Based 1,3-Dipoles: A Modular Approach to Enantioselective 1,3-Dipolar Cycloaddition and Polycyclic 2-Pyrroline Synthesis
• Montréalone [wikipedia]