Organophosphorus compounds (OPCs) are highly important chemicals, finding numerous applications in both academia and industry. Herein we describe a simple photocatalytic method for the stannylation of white phosphorus (P) using a cheap, commercially-available distannane, (BuSn), and anthraquinone as a simple photocatalyst. Subsequent 'one pot' transformation of the resulting stannylated monophosphine intermediate (BuSn)P provides direct, convenient and versatile access to valuable OPCs such as acylated phosphines and tetraalkylphosphonium salts.
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http://dx.doi.org/10.1039/d2cc03474c | DOI Listing |
Chem Commun (Camb)
August 2022
University of Oxford, Department of Chemistry, OX1 3TA, Oxford, UK.
Organophosphorus compounds (OPCs) are highly important chemicals, finding numerous applications in both academia and industry. Herein we describe a simple photocatalytic method for the stannylation of white phosphorus (P) using a cheap, commercially-available distannane, (BuSn), and anthraquinone as a simple photocatalyst. Subsequent 'one pot' transformation of the resulting stannylated monophosphine intermediate (BuSn)P provides direct, convenient and versatile access to valuable OPCs such as acylated phosphines and tetraalkylphosphonium salts.
View Article and Find Full Text PDFJ Org Chem
January 2014
Department of Chemistry, Oregon State University, Corvallis, Oregon 97331-4003, United States.
The "northern" sector of the cembranoid diterpene providencin containing a tetrasubstituted cyclobutane was synthesized from the bis(acetonide) of d-glucose using dicyclopentadienylzirconium(0)-mediated oxygen abstraction from a furanose. Oxidative scission of the vinyl substituent of this cyclobutane gave an aldehyde, which was reacted with an alkynylstannane to provide an allenol. Cyclization of the derived allenone with silver nitrate led to a cyclobutylfuran comprising the northern subunit of providencin.
View Article and Find Full Text PDFDalton Trans
August 2010
Institut für Anorganische Chemie, Goethe-Universität, Max-von-Laue-Str. 7, D-60438, Frankfurt, Germany.
The donor-free mesityllithium was prepared from the reaction of MesBr with n-BuLi in diethyl ether at -78 degrees C. The solid-state structure of unsupported mesityllithium consists of C(2)Li(2)-rings composed of two LiMes units, which interact with adjacent dimers [LiMes](2), forming a polymeric infinite chain along the crystallographic c-axis (monoclinic space group, P2(1)/n). The structure of donor-free mesityllithium reveals short contacts between the C atoms of the mesityl rings and the lithium atoms of neighbouring [LiMes](2) units.
View Article and Find Full Text PDFChem Commun (Camb)
December 2004
Department of Chemistry, Oregon State University, Corvallis, Oregon 97331-4003, USA.
Solvolysis of asymmetric homoallylic triflates bearing a terminal stannyl substituent gives disubstituted cyclopropanes and bicyclopropanes bearing differentiated termini in high enantiopurity.
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