4.7 Article

Palladium-Catalyzed C-N Cross-Coupling of N′-Monosubstituted Sulfondiimines with Aryl Bromides

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 354, Issue 16, Pages 2928-2932

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201200754

Keywords

aryl bromides; cross-coupling; N-arylation; palladium catalysis; sulfondiimines

Funding

  1. Fonds der Chemischen Industrie
  2. Excellence Initiative of the German federal and state governments (Seed Funds at RWTH Aachen University)
  3. Alexander von Humboldt foundation

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A general method for the N-arylation of sulfondiimines with aryl bromides using tris(dibenzylideneacetone)dipalladium(0) [Pd-2(dba)(3)] and 2-dicyclohexylphosphino-2',6'-diisopropoxybiphenyl (RuPhos) as catalyst system was developed. A new benzothiazine was obtained, and a protocol for the cleavage of para-methoxyphenyl (PMP) groups in PMP-protected sulfondiimines has been found, which provides access to synthetically useful NH-derivatives, that are difficult to prepare by other means.

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