Ni-catalyzed highly enantioselective synthesis of sulfur protected P-stereogenic supramolecular phosphine

TitleNi-catalyzed highly enantioselective synthesis of sulfur protected P-stereogenic supramolecular phosphine
Publication TypeJournal Article
Year of Publication2021
AuthorsKoshti(S), VS, Chandanshive, AC, Mote, NR, Chikkali, SH
JournalJournal of Chemical Sciences
Volume133
Issue4
Pagination119
Date PublishedDEC
Type of ArticleArticle
ISSN0974-3626
KeywordsAsymmetric synthesis, Nickel catalyst, P-C coupling, P-Stereogenic phosphine, supramolecular ligands
AbstractAs phosphines readily invert, the synthesis of P-chiral phosphines is a challenging task and has been rarely investigated. We report the synthesis of a nickel complex [Ni-((S,S)Me-FerroLANE)(phenyl)(I)] (Ni-Cat.1) and its performance in a P-C coupling reaction to generate P-chiral phosphine. The Ni-Cat.1 was synthesized by mixing ligand (S,S) Me-FerroLANE with the metal precursor [(diphenylphosphanyl)nickel(phenyl)(I)] in good yield. Ni-Cat.1 was characterized using different spectroscopic and analytical techniques. Treatment of racemic methyl(phenyl)phosphine (1) with 1-(3-iodophenyl)urea (2) produced the corresponding P-chiral supramolecular phosphine (3). Optimization of reaction parameters produced sulfur protected phosphine N-(3-(methyl(phenyl)phosphorothioyl)phenyl)formamide (3') with excellent enantiomeric excess (99% ee) and moderate conversion (51%).
DOI10.1007/s12039-021-01978-3
Type of Journal (Indian or Foreign)Indian
Impact Factor (IF)1.573
Divison category: 
Polymer Science & Engineering

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