Palladium-catalyzed cross-coupling of α-bromocarbonyls and allylic alcohols for the synthesis of α-aryl dicarbonyl compounds† †Electronic supplementary information (ESI) available. CCDC 1042318. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc00505a

نویسندگان

  • Yang Yu
  • Uttam K. Tambar
چکیده

The palladium-catalyzed coupling of olefins and organohalides is a versatile approach for synthesizing complex molecules from simple starting materials. We have developed a palladium-catalyzed coupling of α-bromocarbonyl compounds with allylic alcohols for the generation of acyclic aryl-substituted dicarbonyl compounds. The reaction proceeds via a tandem olefin insertion of an α-acyl radical followed by a 1,2-aryl migration. In addition to providing preliminary evidence for a free radical mediated mechanism, we demonstrate unprecedented levels of 1,3-stereoinduction for the 1,2-migration step.

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منابع مشابه

Dual nickel and Lewis acid catalysis for cross-electrophile coupling: the allylation of aryl halides with allylic alcohols† †Electronic supplementary information (ESI) available. CCDC 1515176. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc03140h

Controlling the selectivity in cross-electrophile coupling reactions is a significant challenge, particularly when one electrophile is much more reactive. We report a general and practical strategy to address this problem in the reaction between reactive and unreactive electrophiles by a combination of nickel and Lewis acid catalysis. This strategy is used for the coupling of aryl halides with ...

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عنوان ژورنال:

دوره 6  شماره 

صفحات  -

تاریخ انتشار 2015