One-Pot Method for Regioselective Bromin­ation and Sequential Carbon-Carbon Bond-Forming Reactions of Allylic Alcohol Derivatives

An efficient one‐pot method for the regioselective bromination of allylic alcohol derivatives (two‐step reaction sequence) followed by Sonogashira, Negishi, or Suzuki–Miyaura coupling reactions in the same reaction vessel (three‐step reaction sequence) has been developed. The key reaction in these o...

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Bibliographic Details
Published in:European journal of organic chemistry 2013-06, Vol.2013 (16), p.3337-3346
Main Authors: Kutsumura, Noriki, Matsubara, Yusuke, Niwa, Kentaro, Ito, Ai, Saito, Takao
Format: Article
Language:English
Subjects:
Alcohol
Allylic compounds
C-C coupling
Cross-coupling
Elimination
Regioselectivity
Synthetic methods
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Summary:An efficient one‐pot method for the regioselective bromination of allylic alcohol derivatives (two‐step reaction sequence) followed by Sonogashira, Negishi, or Suzuki–Miyaura coupling reactions in the same reaction vessel (three‐step reaction sequence) has been developed. The key reaction in these one‐pot systems is the regioselective DBU‐promoted trans HBr elimination of vicinal dibromides bearing an adjacent O‐functional group. Di‐ or trisubstituted olefins were synthesized in high yields with excellent regio‐ and cis–trans selectivities in one‐pot reactions, including a regioselective DBU‐promoted trans HBr elimination. This one‐pot methodology could become a straightforward transformation of “straight” alkenes into “Y‐shaped” alkenes.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201300173