Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 17, Issue -, Pages 866-872Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.17.72
Keywords
(E)-1, 2-bis(diphenylphosphino)ethylene derivative; radical addition; stereoselective phosphinylphosphination; terminal alkyne; tetraphenyldiphosphine monoxide
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Funding
- Japanese Government (Monbukagakusho: MEXT) Scholarship
- JSPS KAKENHI from the Ministry of Education, Culture, Sports, Science and Technology, Japan [19H02791, 19H02756, 19K17746]
- KyotoNAIST Advanced Nanotechnology Network
- Grants-in-Aid for Scientific Research [19H02756, 19H02791, 19K17746] Funding Source: KAKEN
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The study developed a method that can generate pentavalent and trivalent phosphorus-centered radicals simultaneously by homolytic cleavage of the P-V(O)-P-III bond, enabling the phosphinylphosphination of terminal alkynes. This method exhibits high regio- and stereoselectivity and can be applied to a wide range of terminal alkynes.
The homolytic cleavage of the P-V(O)-P-III bond in tetraphenyldiphosphine monoxide simultaneously provides both pentavalent and trivalent phosphorus-centered radicals with different reactivities. The method using V-40 as an initiator is successfully investigated for the regio- and stereoselective phosphinylphosphination of terminal alkynes giving the corresponding trans-isomers of 1-diphenylphosphinyl-2-diphenylthiophosphinyl-1-alkenes in good yields. The protocol can be applied to a wide variety of terminal alkynes including both alkyl-and arylalkynes.
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