Erguven Huseyin, Zhou Cuihan, Arndtsen Bruce A
Department of Chemistry and Chemical Biology, Rutgers University 123 Bevier Road, Piscataway NJ 08854 USA.
Department of Chemistry, McGill University 801 Sherbrooke Street West Montreal QC H3A0B8 Canada
Chem Sci. 2021 Oct 27;12(45):15077-15083. doi: 10.1039/d1sc04088j. eCollection 2021 Nov 24.
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.
通过醛、酰氯与亚磷酸酯PhP(儿茶酚)的多组分反应，可以生成一类新型的含磷1,3 -偶极体。这些1,3 -偶极体形式上是简单维蒂希型叶立德的环状互变异构体，其中儿茶酚 - 亚磷酸酯中的角张力和适度亲核性有利于它们的环化，并且还能引导1,3 -偶极环加成反应，以提供取代产物的单一区域异构体。将偶极体的生成与1,3 -偶极环加成反应相结合，为从可用的醛、酰氯和炔烃组合中制备呋喃提供了一条独特的、模块化的途径，且能独立控制所有四个取代基。
