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Palladium-catalyzed carbon-sulfur or carbon-phosphorus bond metathesis by reversible arylation

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Science  09 Jun 2017:
Vol. 356, Issue 6342, pp. 1059-1063
DOI: 10.1126/science.aam9041

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Teaching sulfur and phosphorus to share

Wouldn't it be nice if real chemistry worked like a modeling kit, and you could just pull a group off one molecule and tack it onto another? Lian et al. report that palladium catalysis can swap aryl rings between pairs of organosulfur or organophosphorus fragments in just this way. They showcase the sulfur swap by breaking down the commercial thermoplastic polyphenylene sulfide into simple monomers.

Science, this issue p. 1059

Abstract

Compounds bearing aryl-sulfur and aryl-phosphorus bonds have found numerous applications in drug development, organic materials, polymer science, and homogeneous catalysis. We describe palladium-catalyzed metathesis reactions of both compound classes, each of which proceeds through a reversible arylation manifold. The synthetic power and immediate utility of this approach are demonstrated in several applications that would be challenging to achieve by means of traditional cross-coupling methods. The C(sp2)–S bond metathesis protocol was used in the depolymerization of a commercial thermoplastic polymer and in the late-stage derivatization of a drug. The C(sp2)–P variant led to the convenient preparation of a variety of phosphorus heterocycles, including a potential chiral ligand and fluorescent organic materials, via a ring-closing transformation.

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