Photochemical transformation of chlorobenzenes and white phosphorus into arylphosphines and phosphonium salts

Marion Till; Verena Streitferdt; Daniel J. Scott; Michael Mende; Ruth Gschwind; Robert Wolf

doi:10.1039/D1CC05691C

Photochemical transformation of chlorobenzenes and white phosphorus into arylphosphines and phosphonium salts

Marion Till, Verena Streitferdt, Daniel J. Scott, Michael Mende, Ruth Gschwind, Robert Wolf

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

20 Citations (SciVal)

Abstract

Chlorobenzenes are important starting materials for the preparation of commercially valuable triarylphosphines and tetraarylphosphonium salts, but their use for the direct arylation of elemental phosphorus has been elusive. Here we describe a simple photochemical route toward such products. UV-LED irradiation (365 nm) of chlorobenzenes, white phosphorus (P₄) and the organic superphotoreductant tetrakis(dimethylamino)ethylene (TDAE) affords the desired arylphosphorus compounds in a single reaction step.

Original language	English
Pages (from-to)	1100-1103
Number of pages	4
Journal	Chemical Communications
Volume	58
Issue number	8
Early online date	6 Dec 2021
DOIs	https://doi.org/10.1039/D1CC05691C
Publication status	Published - 25 Jan 2022

Bibliographical note

Funding Information:
This project received funding from the European Research Council (ERC CoG 772299) and the Deutsche Forschungsge-meinschaft (DFG, CRC 325 Assembly Controlled Chemical Photocatalysis – 444632635 – and RTG 2620 Ion Pair Effects in Molecular Reactivity).

Publisher Copyright:
© The Royal Society of Chemistry.

Access to Document

10.1039/D1CC05691CLicence: CC BY-NC

Cite this

@article{78b543fc84ba43429c24872185a28d02,

title = "Photochemical transformation of chlorobenzenes and white phosphorus into arylphosphines and phosphonium salts",

abstract = "Chlorobenzenes are important starting materials for the preparation of commercially valuable triarylphosphines and tetraarylphosphonium salts, but their use for the direct arylation of elemental phosphorus has been elusive. Here we describe a simple photochemical route toward such products. UV-LED irradiation (365 nm) of chlorobenzenes, white phosphorus (P4) and the organic superphotoreductant tetrakis(dimethylamino)ethylene (TDAE) affords the desired arylphosphorus compounds in a single reaction step.",

author = "Marion Till and Verena Streitferdt and Scott, {Daniel J.} and Michael Mende and Ruth Gschwind and Robert Wolf",

note = "Funding Information: This project received funding from the European Research Council (ERC CoG 772299) and the Deutsche Forschungsge-meinschaft (DFG, CRC 325 Assembly Controlled Chemical Photocatalysis – 444632635 – and RTG 2620 Ion Pair Effects in Molecular Reactivity). Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

year = "2022",

month = jan,

day = "25",

doi = "10.1039/D1CC05691C",

language = "English",

volume = "58",

pages = "1100--1103",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "8",

}

TY - JOUR

T1 - Photochemical transformation of chlorobenzenes and white phosphorus into arylphosphines and phosphonium salts

AU - Till, Marion

AU - Streitferdt, Verena

AU - Scott, Daniel J.

AU - Mende, Michael

AU - Gschwind, Ruth

AU - Wolf, Robert

N1 - Funding Information: This project received funding from the European Research Council (ERC CoG 772299) and the Deutsche Forschungsge-meinschaft (DFG, CRC 325 Assembly Controlled Chemical Photocatalysis – 444632635 – and RTG 2620 Ion Pair Effects in Molecular Reactivity). Publisher Copyright: © The Royal Society of Chemistry.

PY - 2022/1/25

Y1 - 2022/1/25

N2 - Chlorobenzenes are important starting materials for the preparation of commercially valuable triarylphosphines and tetraarylphosphonium salts, but their use for the direct arylation of elemental phosphorus has been elusive. Here we describe a simple photochemical route toward such products. UV-LED irradiation (365 nm) of chlorobenzenes, white phosphorus (P4) and the organic superphotoreductant tetrakis(dimethylamino)ethylene (TDAE) affords the desired arylphosphorus compounds in a single reaction step.

AB - Chlorobenzenes are important starting materials for the preparation of commercially valuable triarylphosphines and tetraarylphosphonium salts, but their use for the direct arylation of elemental phosphorus has been elusive. Here we describe a simple photochemical route toward such products. UV-LED irradiation (365 nm) of chlorobenzenes, white phosphorus (P4) and the organic superphotoreductant tetrakis(dimethylamino)ethylene (TDAE) affords the desired arylphosphorus compounds in a single reaction step.

UR - http://www.scopus.com/inward/record.url?scp=85123589732&partnerID=8YFLogxK

U2 - 10.1039/D1CC05691C

DO - 10.1039/D1CC05691C

M3 - Article

SN - 1359-7345

VL - 58

SP - 1100

EP - 1103

JO - Chemical Communications

JF - Chemical Communications

IS - 8

ER -

Photochemical transformation of chlorobenzenes and white phosphorus into arylphosphines and phosphonium salts

Abstract

Bibliographical note

Access to Document

Other files and links

Fingerprint

Cite this