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ChemInform Abstract: Validating the Alkene and Alkyne Hydrophosphonylation as an Entry to Organophosphonates
- Source :
- ChemInform. 46
- Publication Year :
- 2015
- Publisher :
- Wiley, 2015.
-
Abstract
- The first paper on the hydrophosphonylation of terminal alkenes was published in 1958 by Stiles and coworkers. Afterwards various papers described organometal-catalyzed and free-radical reactions leading to linear anti-Markovnikov adducts and/or branched Markovnikov products. In 1996 Han and Tanaka reported the first example of alkyne hydrophosphonylation catalyzed by a palladium complex. Further studies using other metal catalysts registered poor selectivity as mixtures of adducts were obtained in most of the cases examined. The first example of alkyne hydrophosphonylation by H-phosphonates under free-radical conditions leading to Z- and E-vinylphosphonates in a 1 : 1 ratio was reported by our group. Nevertheless, Z- to E-isomerization took place upon irradiation in the presence of a thiol.
Details
- ISSN :
- 09317597
- Volume :
- 46
- Database :
- OpenAIRE
- Journal :
- ChemInform
- Accession number :
- edsair.doi...........237dc3ecc29c4d1bbe63543484699df3