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

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Lian,  Zhong
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Bhawal,  Benjamin N.
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

Yu,  Peng
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Morandi,  Bill
Research Group Morandi, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Lian, Z., Bhawal, B. N., Yu, P., & Morandi, B. (2017). Palladium-catalyzed carbon-sulfur or carbon-phosphorus bond metathesis by reversible arylation. Science, 356(6342), 1059-1063. doi:10.1126/science.aam9041.


Cite as: https://hdl.handle.net/21.11116/0000-0000-EB8C-A
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.