Nucleophilic H-Phosphites, H-Phosphinates, and H-Phosphine Oxides in Organic Reactions
Abstract P(O)–H compounds like H-phosphites, H-phosphinates, and H-phosphine oxides are widely used as nucleophiles. Herein, their reactions with unsaturated compounds, C–H activation, the Hirao reaction, P–C, P–S, P–O, P–N, and P–F couplings are thoroughly discussed and summarized. This review will...
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Veröffentlicht in: | Synthesis (Stuttgart) 2021-10, Vol.53 (20), p.3683-3698 |
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description | Abstract
P(O)–H compounds like H-phosphites, H-phosphinates, and H-phosphine oxides are widely used as nucleophiles. Herein, their reactions with unsaturated compounds, C–H activation, the Hirao reaction, P–C, P–S, P–O, P–N, and P–F couplings are thoroughly discussed and summarized. This review will focus on their reactions with alkenes, alkynes, enamides, propynoic acids, epoxide, arynes, arenes, quinones, isothiocyanates, diazo compounds, aldehydes, ketones, imines, pyridines, acid derivatives, carbocations, aryl halides, dibromoalkenes, disulfides, thiosulfates, sulfonyl chlorides, iodonium salts, amines, alcohols, and thiols.
1 Introduction
2 Addition to Alkenes/Alkynes
3 Addition to Other Unsaturated Compounds
4 Coupling with Carbocations
5 Phosphorylation of Aryl C–H Bonds
6 Hirao Reaction
7 P–S, P–O, P–N, or P–F Coupling
8 Conclusions |
doi_str_mv | 10.1055/a-1511-0382 |
format | Article |
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P(O)–H compounds like H-phosphites, H-phosphinates, and H-phosphine oxides are widely used as nucleophiles. Herein, their reactions with unsaturated compounds, C–H activation, the Hirao reaction, P–C, P–S, P–O, P–N, and P–F couplings are thoroughly discussed and summarized. This review will focus on their reactions with alkenes, alkynes, enamides, propynoic acids, epoxide, arynes, arenes, quinones, isothiocyanates, diazo compounds, aldehydes, ketones, imines, pyridines, acid derivatives, carbocations, aryl halides, dibromoalkenes, disulfides, thiosulfates, sulfonyl chlorides, iodonium salts, amines, alcohols, and thiols.
1 Introduction
2 Addition to Alkenes/Alkynes
3 Addition to Other Unsaturated Compounds
4 Coupling with Carbocations
5 Phosphorylation of Aryl C–H Bonds
6 Hirao Reaction
7 P–S, P–O, P–N, or P–F Coupling
8 Conclusions</description><identifier>ISSN: 0039-7881</identifier><identifier>EISSN: 1437-210X</identifier><identifier>DOI: 10.1055/a-1511-0382</identifier><language>eng</language><publisher>Rüdigerstraße 14, 70469 Stuttgart, Germany: Georg Thieme Verlag KG</publisher><subject>short review</subject><ispartof>Synthesis (Stuttgart), 2021-10, Vol.53 (20), p.3683-3698</ispartof><rights>Thieme. All rights reserved</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c268t-9e98456d42dd700657632b73912bb062f9eaad55aa5e4c3981a73c67607753d23</citedby><cites>FETCH-LOGICAL-c268t-9e98456d42dd700657632b73912bb062f9eaad55aa5e4c3981a73c67607753d23</cites><orcidid>0000-0002-6107-1019</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/a-1511-0382.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/a-1511-0382$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,780,784,3017,3018,27924,27925,54559,54560</link.rule.ids></links><search><creatorcontrib>Wang, Zhan-Yong</creatorcontrib><creatorcontrib>Guo, Qi</creatorcontrib><creatorcontrib>Xu, Shaohong</creatorcontrib><creatorcontrib>Wang, Kai-Kai</creatorcontrib><title>Nucleophilic H-Phosphites, H-Phosphinates, and H-Phosphine Oxides in Organic Reactions</title><title>Synthesis (Stuttgart)</title><addtitle>Synthesis</addtitle><description>Abstract
P(O)–H compounds like H-phosphites, H-phosphinates, and H-phosphine oxides are widely used as nucleophiles. Herein, their reactions with unsaturated compounds, C–H activation, the Hirao reaction, P–C, P–S, P–O, P–N, and P–F couplings are thoroughly discussed and summarized. This review will focus on their reactions with alkenes, alkynes, enamides, propynoic acids, epoxide, arynes, arenes, quinones, isothiocyanates, diazo compounds, aldehydes, ketones, imines, pyridines, acid derivatives, carbocations, aryl halides, dibromoalkenes, disulfides, thiosulfates, sulfonyl chlorides, iodonium salts, amines, alcohols, and thiols.
1 Introduction
2 Addition to Alkenes/Alkynes
3 Addition to Other Unsaturated Compounds
4 Coupling with Carbocations
5 Phosphorylation of Aryl C–H Bonds
6 Hirao Reaction
7 P–S, P–O, P–N, or P–F Coupling
8 Conclusions</description><subject>short review</subject><issn>0039-7881</issn><issn>1437-210X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNptkMFKAzEQhoMoWKsnX2DPanSSbJLNUYpaobgiKt7CbJLalHa3bLagb--uFfTgafiG7x-Gn5BTBpcMpLxCyiRjFETB98iI5UJTzuBtn4wAhKG6KNghOUppCQCaCzMirw9btwrNZhFX0WVT-rhoUg9dSBe_VOM3Y-3_7EJWfkQfUhbrrGzfse7zTwFdF5s6HZODOa5SOPmZY_Jye_M8mdJZeXc_uZ5Rx1XRURNMkUvlc-69BlBSK8ErLQzjVQWKz01A9FIiypA7YQqGWjilFWgthediTM53d13bpNSGud20cY3tp2Vgh0os2qESO1TS22c7u1vEsA522Wzbun_vX_kLSwZgAQ</recordid><startdate>20211019</startdate><enddate>20211019</enddate><creator>Wang, Zhan-Yong</creator><creator>Guo, Qi</creator><creator>Xu, Shaohong</creator><creator>Wang, Kai-Kai</creator><general>Georg Thieme Verlag KG</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-6107-1019</orcidid></search><sort><creationdate>20211019</creationdate><title>Nucleophilic H-Phosphites, H-Phosphinates, and H-Phosphine Oxides in Organic Reactions</title><author>Wang, Zhan-Yong ; Guo, Qi ; Xu, Shaohong ; Wang, Kai-Kai</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c268t-9e98456d42dd700657632b73912bb062f9eaad55aa5e4c3981a73c67607753d23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>short review</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Zhan-Yong</creatorcontrib><creatorcontrib>Guo, Qi</creatorcontrib><creatorcontrib>Xu, Shaohong</creatorcontrib><creatorcontrib>Wang, Kai-Kai</creatorcontrib><collection>CrossRef</collection><jtitle>Synthesis (Stuttgart)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Zhan-Yong</au><au>Guo, Qi</au><au>Xu, Shaohong</au><au>Wang, Kai-Kai</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Nucleophilic H-Phosphites, H-Phosphinates, and H-Phosphine Oxides in Organic Reactions</atitle><jtitle>Synthesis (Stuttgart)</jtitle><addtitle>Synthesis</addtitle><date>2021-10-19</date><risdate>2021</risdate><volume>53</volume><issue>20</issue><spage>3683</spage><epage>3698</epage><pages>3683-3698</pages><issn>0039-7881</issn><eissn>1437-210X</eissn><abstract>Abstract
P(O)–H compounds like H-phosphites, H-phosphinates, and H-phosphine oxides are widely used as nucleophiles. Herein, their reactions with unsaturated compounds, C–H activation, the Hirao reaction, P–C, P–S, P–O, P–N, and P–F couplings are thoroughly discussed and summarized. This review will focus on their reactions with alkenes, alkynes, enamides, propynoic acids, epoxide, arynes, arenes, quinones, isothiocyanates, diazo compounds, aldehydes, ketones, imines, pyridines, acid derivatives, carbocations, aryl halides, dibromoalkenes, disulfides, thiosulfates, sulfonyl chlorides, iodonium salts, amines, alcohols, and thiols.
1 Introduction
2 Addition to Alkenes/Alkynes
3 Addition to Other Unsaturated Compounds
4 Coupling with Carbocations
5 Phosphorylation of Aryl C–H Bonds
6 Hirao Reaction
7 P–S, P–O, P–N, or P–F Coupling
8 Conclusions</abstract><cop>Rüdigerstraße 14, 70469 Stuttgart, Germany</cop><pub>Georg Thieme Verlag KG</pub><doi>10.1055/a-1511-0382</doi><tpages>16</tpages><orcidid>https://orcid.org/0000-0002-6107-1019</orcidid></addata></record> |
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title | Nucleophilic H-Phosphites, H-Phosphinates, and H-Phosphine Oxides in Organic Reactions |
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