Highly regio- and stereoselective phosphinylphosphination of terminal alkynes with tetraphenyldiphosphine monoxide under radical conditions

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Tran, Dat Phuc, Sato, Yuki, Yamamoto, Yuki, Kawaguchi, Shin-ichi, Kodama, Shintaro, Nomoto, Akihiro, Ogawa, Akiya
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2021
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8077611/
https://www.ncbi.nlm.nih.gov/pubmed/33968259
http://dx.doi.org/10.3762/bjoc.17.72
_version_ 1783684910768193536
author Tran, Dat Phuc
Sato, Yuki
Yamamoto, Yuki
Kawaguchi, Shin-ichi
Kodama, Shintaro
Nomoto, Akihiro
Ogawa, Akiya
author_facet Tran, Dat Phuc
Sato, Yuki
Yamamoto, Yuki
Kawaguchi, Shin-ichi
Kodama, Shintaro
Nomoto, Akihiro
Ogawa, Akiya
author_sort Tran, Dat Phuc
collection PubMed
description 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.
format Online
Article
Text
id pubmed-8077611
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-80776112021-05-06 Highly regio- and stereoselective phosphinylphosphination of terminal alkynes with tetraphenyldiphosphine monoxide under radical conditions Tran, Dat Phuc Sato, Yuki Yamamoto, Yuki Kawaguchi, Shin-ichi Kodama, Shintaro Nomoto, Akihiro Ogawa, Akiya Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2021-04-20 /pmc/articles/PMC8077611/ /pubmed/33968259 http://dx.doi.org/10.3762/bjoc.17.72 Text en Copyright © 2021, Tran et al. https://creativecommons.org/licenses/by/4.0/https://www.beilstein-journals.org/bjoc/terms/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). Please note that the reuse, redistribution and reproduction in particular requires that the author(s) and source are credited and that individual graphics may be subject to special legal provisions. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms/terms)
spellingShingle Full Research Paper
Tran, Dat Phuc
Sato, Yuki
Yamamoto, Yuki
Kawaguchi, Shin-ichi
Kodama, Shintaro
Nomoto, Akihiro
Ogawa, Akiya
Highly regio- and stereoselective phosphinylphosphination of terminal alkynes with tetraphenyldiphosphine monoxide under radical conditions
title Highly regio- and stereoselective phosphinylphosphination of terminal alkynes with tetraphenyldiphosphine monoxide under radical conditions
title_full Highly regio- and stereoselective phosphinylphosphination of terminal alkynes with tetraphenyldiphosphine monoxide under radical conditions
title_fullStr Highly regio- and stereoselective phosphinylphosphination of terminal alkynes with tetraphenyldiphosphine monoxide under radical conditions
title_full_unstemmed Highly regio- and stereoselective phosphinylphosphination of terminal alkynes with tetraphenyldiphosphine monoxide under radical conditions
title_short Highly regio- and stereoselective phosphinylphosphination of terminal alkynes with tetraphenyldiphosphine monoxide under radical conditions
title_sort highly regio- and stereoselective phosphinylphosphination of terminal alkynes with tetraphenyldiphosphine monoxide under radical conditions
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8077611/
https://www.ncbi.nlm.nih.gov/pubmed/33968259
http://dx.doi.org/10.3762/bjoc.17.72
work_keys_str_mv AT trandatphuc highlyregioandstereoselectivephosphinylphosphinationofterminalalkyneswithtetraphenyldiphosphinemonoxideunderradicalconditions
AT satoyuki highlyregioandstereoselectivephosphinylphosphinationofterminalalkyneswithtetraphenyldiphosphinemonoxideunderradicalconditions
AT yamamotoyuki highlyregioandstereoselectivephosphinylphosphinationofterminalalkyneswithtetraphenyldiphosphinemonoxideunderradicalconditions
AT kawaguchishinichi highlyregioandstereoselectivephosphinylphosphinationofterminalalkyneswithtetraphenyldiphosphinemonoxideunderradicalconditions
AT kodamashintaro highlyregioandstereoselectivephosphinylphosphinationofterminalalkyneswithtetraphenyldiphosphinemonoxideunderradicalconditions
AT nomotoakihiro highlyregioandstereoselectivephosphinylphosphinationofterminalalkyneswithtetraphenyldiphosphinemonoxideunderradicalconditions
AT ogawaakiya highlyregioandstereoselectivephosphinylphosphinationofterminalalkyneswithtetraphenyldiphosphinemonoxideunderradicalconditions

Ejemplares similares