A novel and convenient protocol for synthesis of alpha-haloacrylates.
A novel and convenient protocol for synthesis of alpha-haloacrylates starting from phosphonium ylide and aldedyde or alcohol was described. Halodimethylsulfonium halide was used for the first time in halogenation of phosphonium ylide. Good yield as well as a high Z/E ratio were shown in representative cases, and an umpolung dimethyl sulfide-ylide species might be involved as an intermediate.
Jiang
Biao
B
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 354 Fenglin Road, Shanghai 200032, PR China. jiangb@mail.sioc.ac.cn
Dou
Ying
Y
Xu
Xiangya
X
Xu
Min
M
D000179:Acrylates / Q000138:chemical synthesis* / Q000737:chemistry; D000438:Alcohols / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000179:Acrylates; D000438:Alcohols; D000447:Aldehydes; D000475:Alkenes; D006846:Hydrocarbons, Halogenated