title: One-pot synthesis of alpha-iodo-substituted alpha,beta-unsaturated aldehydes from propargylic alcohols.
abstract: An efficient one-pot method for the preparation of alpha-iodo-substituted alpha,beta-unsaturated aldehydes (alpha-iodoenals) from propargylic alcohol is developed. The reaction proceeds via an iodoallene intermediate, which is generated in situ by the reaction of propargylic alcohol with aqueous HI. The iodoallene intermediate is further transformed to an alpha-iodoenal derivative in good overall yield by oxidation with molecular O(2).
authors.affiliation: Beijing National Laboratory of Molecular Sciences (BNLMS), Green Chemistry Center (GCC), and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China.
authors.forename: Shufeng
authors.initials: S
authors.lastname: Chen
authors.forename: Jianbo
authors.initials: J
authors.lastname: Wang
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000466:Alkadienes / Q000737:chemistry; D000478:Alkylation; D000480:Alkynes / Q000737:chemistry*; D017605:Bromine Compounds / Q000138:chemical synthesis / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D020005:Propanols / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000466:Alkadienes; D000480:Alkynes; D017605:Bromine Compounds; D007211:Indoles; D020005:Propanols; C025947:propadiene; C028255:propargyl alcohol