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

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.

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

http://science.sciencemag.org/content/356/6342/1059

Update time:2017/6/19 Author:admin Hit:12【Print