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. 2021 Oct 27;12(45):15077-15083.
doi: 10.1039/d1sc04088j. eCollection 2021 Nov 24.

Multicomponent formation route to a new class of oxygen-based 1,3-dipoles and the modular synthesis of furans

Huseyin Erguven  1 , Cuihan Zhou  2 , Bruce A Arndtsen  2
Affiliations

Multicomponent formation route to a new class of oxygen-based 1,3-dipoles and the modular synthesis of furans

Huseyin Erguven et al. Chem Sci. .

Abstract

A new class of phosphorus-containing 1,3-dipoles can be generated by the multicomponent reaction of aldehydes, acid chlorides and the phosphonite PhP(catechyl). These 1,3-dipoles are formally cyclic tautomers of simple Wittig-type ylides, where the angle strain and moderate nucleophilicity in the catechyl-phosphonite favor their cyclization and also direct 1,3-dipolar cycloaddition to afford single regioisomers of substituted products. Coupling the generation of the dipoles with 1,3-dipolar cycloaddition offers a unique, modular route to furans from combinations of available aldehydes, acid chlorides and alkynes with independent control of all four substituents.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Cycloaddition approaches to furan derivatives and design of a new phosphorus-based 1,3-dipolar cycloaddition reagent.
Fig. 2
Fig. 2. Characterization of the phosphorus-containing 1,3-dipole 1.
Fig. 3
Fig. 3. Synthesis of oligomeric furans and oxazoles via 1,3-dipolar cycloaddition with 1.
See this image and copyright information in PMC

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