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

Autor: Lian Z; Max-Planck-Institut für Kohlenforschung, 45470 Mülheim an der Ruhr, Germany., Bhawal BN; Max-Planck-Institut für Kohlenforschung, 45470 Mülheim an der Ruhr, Germany., Yu P; Max-Planck-Institut für Kohlenforschung, 45470 Mülheim an der Ruhr, Germany., Morandi B; Max-Planck-Institut für Kohlenforschung, 45470 Mülheim an der Ruhr, Germany. morandi@kofo.mpg.de.
Jazyk: angličtina
Zdroj: Science (New York, N.Y.) [Science] 2017 Jun 09; Vol. 356 (6342), pp. 1059-1063.
DOI: 10.1126/science.aam9041
Abstrakt: 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(sp 2 )-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(sp 2 )-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.
(Copyright © 2017, American Association for the Advancement of Science.)
Databáze: MEDLINE
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