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One-Pot Synthesis of 1-Iodoalkynes and Trisubstituted Alkenes from Benzylic and Allylic Bromides

  作者 PELLETIER GUILLAUME; LIE SHARON; MOUSSEAU JAMES J; CHARETTE ANDRE B  
  选自 期刊  Organic Letters;  卷期  2012年14-21;  页码  5464-5467  
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[摘要]1-Iodoalkynes are formed in moderate to high yields from readily accessible benzylic and allylic alkyl bromides by a one-pot homologation/double elimination procedure with iodoform (CHI3). The developed conditions include facile purification and avoid the use of an excess of triphenylphosphine (PPh3), as described in classical Corey-Fuchs iodoalkynylation conditions. Replacing CHI3 with CHI2CI allows the isolation of the corresponding gem-(2)-chloro-(E)-iodoalkene in good yield and stereoselectivity. Moreover, the use of benzhydryl bromides as nucleophiles enables the synthesis of trisubstituted alkenes under similar reaction conditions.

 
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