Cobalt-Catalyzed Markovnikov-Selective Radical Hydroacylation of Unactivated Alkenes with Acylphosphonates
Acylphosphonates having the 5,5-dimethyl-1,3,2-dioxophosphinanyl skeleton are developed as efficient intermolecular radical acylation reagents, which enable the cobalt-catalyzed Markovnikov hydroacylation of unactivated alkenes at room temperature under mild conditions. The protocol exhibits broad substrate scope and wide functional group compatibility, providing branched ketones in satisfactory yields. A mechanism involving the Co-H mediated hydrogen atom transfer and subsequent trapping of alkyl radicals by acylphosphonates is proposed.
Synthesis of new α-hydroxy-, α-halogeno- and vinylphosphonates derived from 5,5-dimethyl-1,3,2-dioxaphosphinan-2-one
Several α-hydroxyphosphonates have been prepared by the Pudovik reaction of the cyclic phosphite 5,5-dimethyl-1,3,2-dioxaphosphinan-2-one with aldehydes and β-oxo aldehydes. These can be readily converted to α-chloro- or α-bromophosphonates in excellent yield by simply treating them with thionyl chloride or bromide. Reaction with phosphorus triiodide gave α-iodophosphonates and α-hydridophosphonates. The Pudovik products obtained from β-oxo aldehydes can be readily dehydrated to give vinylphosphonates.
Kumaraswamy, Sudha,Selvi, R. Senthamizh,Swamy, K. C. Kumara
p. 207 - 212
(2007/10/03)
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