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Article

Palladium-Catalyzed N-Arylation of Sulfoximines with Aryl Bromides and Aryl Iodides

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Carsten Bolm* and Jens P. Hildebrand

Institut fr Organische Chemie der RWTH Aachen, Prof.-Pirlet-Strasse 1, D-52056 Aachen, Germany

J. Org. Chem., 2000, 65 (1), pp 169–175

DOI: 10.1021/jo991342u

Publication Date (Web): December 17, 1999

E-mail: Carsten.Bolm@oc.rwth-aachen.de. Fax: (Int.) +49 241 8888 391. Tel: (Int.) +49 241 80 4675.

Abstract

Various N-arylated sulfoximines have been synthesized in high yield by a direct approach which is based on a palladium-catalyzed cross-coupling strategy. Aryl bromides of variable substitution pattern were found to be the most effective coupling partners, whereas aryl iodides showed a nonpredictable behavior requiring lithium or silver salts as additives to ensure product formation in acceptable yields. Coupling of (S)-2-(2‘-bromophenyl)-4-tert-butyloxazoline with enantiomerically pure (−)-(RS)-S-methyl-S-phenylsulfoximine afforded the corresponding product in good yield as a single diastereomer, showing that the palladium-catalyzed arylation proceeds in a stereospecific manner. The reaction with dibromobenzenes yielded the monosulfonimidoyl arenes in all cases, suggesting that the introduction of the sulfonimidoyl moiety deactivates the arene, thus preventing a second coupling step.

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Published In Issue January 14, 2000
Received August 24, 1999

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Article

Palladium-Catalyzed N-Arylation of Sulfoximines with Aryl Bromides and Aryl Iodides