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Synthesis 2018; 50(17): 3402-3407
DOI: 10.1055/s-0037-1609447
DOI: 10.1055/s-0037-1609447
special topic
Bromine Cation Initiated vic-Diphosphination of Styrenes with Diphosphines under Photoredox Catalysis
This work was supported by JSPS KAKENHI Grant Nos. JP 15H05485 (Grant-in-Aid for Young Scientists (A)) to K.H. and JP 17H06092 (Grant-in-Aid for Specially Promoted Research) to M.M.Further Information
Publication History
Received: 19 January 2018
Accepted after revision: 13 March 2018
Publication Date:
04 April 2018 (online)
Published as part of the Special Topic Photoredox Methods and their Strategic Applications in Synthesis
Abstract
An N-bromosuccinimide (NBS)-initiated vic-diphosphination of styrenes with diphosphines proceeds under visible-light-promoted Ir(ppy)3 photoredox catalysis to deliver the corresponding 1,2-diphosphinoethane derivatives in good yields. The NBS is a bromine cation source and generates a bromophosphine, which undergoes a single-electron reduction by the excited iridium species to form phosphinyl radicals of key species in the diphoshination reaction. The newly developed photoredox catalysis demonstrates better reaction efficiency, functional group compatibility, and scalability than the previous photocatalysis using N-fluorobenzenesulfonimide (NFSI) and silylphosphine.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609447.
- Supporting Information
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A recent review:
Limited successful examples with special reagents or harsh conditions:
A related double hydrophosphination of alkynes to DPPE-type ligand:
Selected reviews on visible-light-promoted photoredox catalysis:
Recent advances in organophosphorus chemistry under photoredox catalysis:
The in situ generation of a MeOTf adduct (phosphonium cation) can be supported by observation of a characteristic large 1 J PP coupling (ca. 300 Hz) in 31P{1H} NMR studies. See the Supporting Information for details. Also see:
The obtained phosphine sulfides can be readily desulfidated to the corresponding phosphines: