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Photocatalytic Arylation of P 4 and PH 3 : Reaction Development Through Mechanistic Insight
Detailed 31 P{ 1 H} NMR spectroscopic investigations provide deeper insight into the complex, multi‐step mechanisms involved in the recently reported photocatalytic arylation of white phosphorus (P 4 ). Specifically, these studies have identified a number of previously unrecognized side products, wh...
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| Published in: | Angewandte Chemie 2021-11, Vol.133 (46), p.24855-24863 |
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| Main Authors: | , , , , , , , |
| Format: | Article |
| Language: | English |
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| cites | cdi_FETCH-LOGICAL-c849-cc16aaf943232b2b25a5e15f946fd0aa5e8b25c78ed4a1f0ac476529c2a4d7593 |
| container_end_page | 24863 |
| container_issue | 46 |
| container_start_page | 24855 |
| container_title | Angewandte Chemie |
| container_volume | 133 |
| creator | Rothfelder, Robin Streitferdt, Verena Lennert, Ulrich Cammarata, Jose Scott, Daniel J. Zeitler, Kirsten Gschwind, Ruth M. Wolf, Robert |
| description | Detailed
31
P{
1
H} NMR spectroscopic investigations provide deeper insight into the complex, multi‐step mechanisms involved in the recently reported photocatalytic arylation of white phosphorus (P
4
). Specifically, these studies have identified a number of previously unrecognized side products, which arise from an unexpected non‐innocent behavior of the commonly employed terminal reductant Et
3
N. The different rate of formation of these products explains discrepancies in the performance of the two most effective catalysts, [Ir(dtbbpy)(ppy)
2
][PF
6
] (dtbbpy=4,4′‐di‐
tert
‐butyl‐2,2′‐bipyridine) and 3DPAFIPN. Inspired by the observation of PH
3
as a minor intermediate, we have developed the first catalytic procedure for the arylation of this key industrial compound. Similar to P
4
arylation, this method affords valuable triarylphosphines or tetraarylphosphonium salts depending on the steric profile of the aryl substituents. |
| doi_str_mv | 10.1002/ange.202110619 |
| format | article |
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31
P{
1
H} NMR spectroscopic investigations provide deeper insight into the complex, multi‐step mechanisms involved in the recently reported photocatalytic arylation of white phosphorus (P
4
). Specifically, these studies have identified a number of previously unrecognized side products, which arise from an unexpected non‐innocent behavior of the commonly employed terminal reductant Et
3
N. The different rate of formation of these products explains discrepancies in the performance of the two most effective catalysts, [Ir(dtbbpy)(ppy)
2
][PF
6
] (dtbbpy=4,4′‐di‐
tert
‐butyl‐2,2′‐bipyridine) and 3DPAFIPN. Inspired by the observation of PH
3
as a minor intermediate, we have developed the first catalytic procedure for the arylation of this key industrial compound. Similar to P
4
arylation, this method affords valuable triarylphosphines or tetraarylphosphonium salts depending on the steric profile of the aryl substituents.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.202110619</identifier><language>eng</language><ispartof>Angewandte Chemie, 2021-11, Vol.133 (46), p.24855-24863</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c849-cc16aaf943232b2b25a5e15f946fd0aa5e8b25c78ed4a1f0ac476529c2a4d7593</citedby><cites>FETCH-LOGICAL-c849-cc16aaf943232b2b25a5e15f946fd0aa5e8b25c78ed4a1f0ac476529c2a4d7593</cites><orcidid>0000-0003-1549-5002 ; 0000-0003-3052-0077 ; 0000-0001-7826-9833 ; 0000-0003-4066-6483</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Rothfelder, Robin</creatorcontrib><creatorcontrib>Streitferdt, Verena</creatorcontrib><creatorcontrib>Lennert, Ulrich</creatorcontrib><creatorcontrib>Cammarata, Jose</creatorcontrib><creatorcontrib>Scott, Daniel J.</creatorcontrib><creatorcontrib>Zeitler, Kirsten</creatorcontrib><creatorcontrib>Gschwind, Ruth M.</creatorcontrib><creatorcontrib>Wolf, Robert</creatorcontrib><title>Photocatalytic Arylation of P 4 and PH 3 : Reaction Development Through Mechanistic Insight</title><title>Angewandte Chemie</title><description>Detailed
31
P{
1
H} NMR spectroscopic investigations provide deeper insight into the complex, multi‐step mechanisms involved in the recently reported photocatalytic arylation of white phosphorus (P
4
). Specifically, these studies have identified a number of previously unrecognized side products, which arise from an unexpected non‐innocent behavior of the commonly employed terminal reductant Et
3
N. The different rate of formation of these products explains discrepancies in the performance of the two most effective catalysts, [Ir(dtbbpy)(ppy)
2
][PF
6
] (dtbbpy=4,4′‐di‐
tert
‐butyl‐2,2′‐bipyridine) and 3DPAFIPN. Inspired by the observation of PH
3
as a minor intermediate, we have developed the first catalytic procedure for the arylation of this key industrial compound. Similar to P
4
arylation, this method affords valuable triarylphosphines or tetraarylphosphonium salts depending on the steric profile of the aryl substituents.</description><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNo9kE1LxDAYhIMoWFevnvMHWt-kSdt4W1bdXVixSG8eymuafki3WZIq9N_bqsgchpmBOTyE3DKIGAC_w6ExEQfOGCRMnZGASc7COJXpOQkAhAgzLtQlufL-AwASnqqAvOWtHa3GEftp7DRdu6nHsbMDtTXNqaA4VDTf0Zje01eD-md6MF-mt6ejGUZatM5-Ni19NrrFofPLyX7wXdOO1-Sixt6bmz9fkeLpsdjswsPLdr9ZH0KdCRVqzRLEWomYx_x9lkRpmJyLpK4A55DNnU4zUwlkNaAWaSK50hxFlUoVr0j0e6ud9d6Zujy57ohuKhmUC5lyIVP-k4m_AU8CVu4</recordid><startdate>20211108</startdate><enddate>20211108</enddate><creator>Rothfelder, Robin</creator><creator>Streitferdt, Verena</creator><creator>Lennert, Ulrich</creator><creator>Cammarata, Jose</creator><creator>Scott, Daniel J.</creator><creator>Zeitler, Kirsten</creator><creator>Gschwind, Ruth M.</creator><creator>Wolf, Robert</creator><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-1549-5002</orcidid><orcidid>https://orcid.org/0000-0003-3052-0077</orcidid><orcidid>https://orcid.org/0000-0001-7826-9833</orcidid><orcidid>https://orcid.org/0000-0003-4066-6483</orcidid></search><sort><creationdate>20211108</creationdate><title>Photocatalytic Arylation of P 4 and PH 3 : Reaction Development Through Mechanistic Insight</title><author>Rothfelder, Robin ; Streitferdt, Verena ; Lennert, Ulrich ; Cammarata, Jose ; Scott, Daniel J. ; Zeitler, Kirsten ; Gschwind, Ruth M. ; Wolf, Robert</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c849-cc16aaf943232b2b25a5e15f946fd0aa5e8b25c78ed4a1f0ac476529c2a4d7593</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rothfelder, Robin</creatorcontrib><creatorcontrib>Streitferdt, Verena</creatorcontrib><creatorcontrib>Lennert, Ulrich</creatorcontrib><creatorcontrib>Cammarata, Jose</creatorcontrib><creatorcontrib>Scott, Daniel J.</creatorcontrib><creatorcontrib>Zeitler, Kirsten</creatorcontrib><creatorcontrib>Gschwind, Ruth M.</creatorcontrib><creatorcontrib>Wolf, Robert</creatorcontrib><collection>CrossRef</collection><jtitle>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rothfelder, Robin</au><au>Streitferdt, Verena</au><au>Lennert, Ulrich</au><au>Cammarata, Jose</au><au>Scott, Daniel J.</au><au>Zeitler, Kirsten</au><au>Gschwind, Ruth M.</au><au>Wolf, Robert</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photocatalytic Arylation of P 4 and PH 3 : Reaction Development Through Mechanistic Insight</atitle><jtitle>Angewandte Chemie</jtitle><date>2021-11-08</date><risdate>2021</risdate><volume>133</volume><issue>46</issue><spage>24855</spage><epage>24863</epage><pages>24855-24863</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>Detailed
31
P{
1
H} NMR spectroscopic investigations provide deeper insight into the complex, multi‐step mechanisms involved in the recently reported photocatalytic arylation of white phosphorus (P
4
). Specifically, these studies have identified a number of previously unrecognized side products, which arise from an unexpected non‐innocent behavior of the commonly employed terminal reductant Et
3
N. The different rate of formation of these products explains discrepancies in the performance of the two most effective catalysts, [Ir(dtbbpy)(ppy)
2
][PF
6
] (dtbbpy=4,4′‐di‐
tert
‐butyl‐2,2′‐bipyridine) and 3DPAFIPN. Inspired by the observation of PH
3
as a minor intermediate, we have developed the first catalytic procedure for the arylation of this key industrial compound. Similar to P
4
arylation, this method affords valuable triarylphosphines or tetraarylphosphonium salts depending on the steric profile of the aryl substituents.</abstract><doi>10.1002/ange.202110619</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0003-1549-5002</orcidid><orcidid>https://orcid.org/0000-0003-3052-0077</orcidid><orcidid>https://orcid.org/0000-0001-7826-9833</orcidid><orcidid>https://orcid.org/0000-0003-4066-6483</orcidid></addata></record> |
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| issn | 0044-8249 1521-3757 |
| language | eng |
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| source | Wiley |
| title | Photocatalytic Arylation of P 4 and PH 3 : Reaction Development Through Mechanistic Insight |
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