Photocatalytic dual decarboxylative alkenylation mediated by triphenylphosphine and sodium iodide
An efficient photocatalytic dual decarboxylative alkenylation of α,β-unsaturated carboxylic acids and alkyl N -hydroxyphthalimide (NHP) esters mediated by triphenylphosphine and sodium iodide has been developed. This protocol proceeds under 456-nanometer irradiation by visible blue light in the abse...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2020-08, Vol.18 (29), p.5589-5593 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Wang, Hong-Yu Zhong, Long-Jin Lv, Gui-Fen Li, Yang Li, Jin-Heng |
| description | An efficient photocatalytic dual decarboxylative alkenylation of α,β-unsaturated carboxylic acids and alkyl
N
-hydroxyphthalimide (NHP) esters mediated by triphenylphosphine and sodium iodide has been developed. This protocol proceeds under 456-nanometer irradiation by visible blue light in the absence of transition metals or organic dye based photoredox catalysts. The reaction is successfully applied to a wide range of redox-active esters derived from aliphatic carboxylic acids (1°, 2° and 3°) and α-amino acids, enabling transformations of diverse α,β-unsaturated carboxylic acids to α,β-alkylated styrenes with high efficiency and excellent selectivity under mild conditions.
A new transition-metal-free photoredox decarboxylative alkylation of α,β-unsaturated carboxylic acids and alkyl
N
-hydroxyphthalimide (NHP) esters by NaI/PPh
3
catalysis has been developed. |
| doi_str_mv | 10.1039/d0ob01242d |
| format | Article |
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N
-hydroxyphthalimide (NHP) esters mediated by triphenylphosphine and sodium iodide has been developed. This protocol proceeds under 456-nanometer irradiation by visible blue light in the absence of transition metals or organic dye based photoredox catalysts. The reaction is successfully applied to a wide range of redox-active esters derived from aliphatic carboxylic acids (1°, 2° and 3°) and α-amino acids, enabling transformations of diverse α,β-unsaturated carboxylic acids to α,β-alkylated styrenes with high efficiency and excellent selectivity under mild conditions.
A new transition-metal-free photoredox decarboxylative alkylation of α,β-unsaturated carboxylic acids and alkyl
N
-hydroxyphthalimide (NHP) esters by NaI/PPh
3
catalysis has been developed.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d0ob01242d</identifier><identifier>PMID: 32677630</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Aliphatic compounds ; Alkylation ; Amino acids ; Carboxylic acids ; Catalysts ; Esters ; Iodides ; Irradiation ; Photocatalysis ; Photoredox catalysis ; Selectivity ; Sodium ; Sodium iodide ; Styrenes ; Transition metals</subject><ispartof>Organic & biomolecular chemistry, 2020-08, Vol.18 (29), p.5589-5593</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c363t-f17a8ad1bac67de3c8b8de3a8614b429eaee3268cc07113f9aee789a18094cd63</citedby><cites>FETCH-LOGICAL-c363t-f17a8ad1bac67de3c8b8de3a8614b429eaee3268cc07113f9aee789a18094cd63</cites><orcidid>0000-0001-6026-4794 ; 0000-0001-7215-7152</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/32677630$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Hong-Yu</creatorcontrib><creatorcontrib>Zhong, Long-Jin</creatorcontrib><creatorcontrib>Lv, Gui-Fen</creatorcontrib><creatorcontrib>Li, Yang</creatorcontrib><creatorcontrib>Li, Jin-Heng</creatorcontrib><title>Photocatalytic dual decarboxylative alkenylation mediated by triphenylphosphine and sodium iodide</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>An efficient photocatalytic dual decarboxylative alkenylation of α,β-unsaturated carboxylic acids and alkyl
N
-hydroxyphthalimide (NHP) esters mediated by triphenylphosphine and sodium iodide has been developed. This protocol proceeds under 456-nanometer irradiation by visible blue light in the absence of transition metals or organic dye based photoredox catalysts. The reaction is successfully applied to a wide range of redox-active esters derived from aliphatic carboxylic acids (1°, 2° and 3°) and α-amino acids, enabling transformations of diverse α,β-unsaturated carboxylic acids to α,β-alkylated styrenes with high efficiency and excellent selectivity under mild conditions.
A new transition-metal-free photoredox decarboxylative alkylation of α,β-unsaturated carboxylic acids and alkyl
N
-hydroxyphthalimide (NHP) esters by NaI/PPh
3
catalysis has been developed.</description><subject>Aliphatic compounds</subject><subject>Alkylation</subject><subject>Amino acids</subject><subject>Carboxylic acids</subject><subject>Catalysts</subject><subject>Esters</subject><subject>Iodides</subject><subject>Irradiation</subject><subject>Photocatalysis</subject><subject>Photoredox catalysis</subject><subject>Selectivity</subject><subject>Sodium</subject><subject>Sodium iodide</subject><subject>Styrenes</subject><subject>Transition metals</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp90c9LwzAUB_AgipvTi3el4kWEatLUpjnq5i8YzIOey2uSssyuqUkr9r833eYED55eHu_D4_ENQscEXxFM-bXEJsckiiO5g4YkZizEN5Tvbt8RHqAD5xYYE86SeB8NaJQwllA8RPAyN40R0EDZNVoEsoUykEqAzc1XV0KjP1UA5buqVo2pgqWSGholg7wLGqvreT-q58bVc115W8nAGanbZaB9keoQ7RVQOnW0qSP09nD_On4Kp7PH5_HtNBQ0oU1YEAYpSJKDSJhUVKR56gukCYnzOOIKlPJnp0JgRggtuO9ZyoGkmMdCJnSELtZ7a2s-WuWabKmdUGUJlTKty3w-MeeMYerp-R-6MK2t_HW9YjxNejZCl2slrHHOqiKrrV6C7TKCsz74bIJnd6vgJx6fbla2uU9oS3-S9uBsDawT2-nvz2W1LLw5-c_Qb_y1lQU</recordid><startdate>20200807</startdate><enddate>20200807</enddate><creator>Wang, Hong-Yu</creator><creator>Zhong, Long-Jin</creator><creator>Lv, Gui-Fen</creator><creator>Li, Yang</creator><creator>Li, Jin-Heng</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-6026-4794</orcidid><orcidid>https://orcid.org/0000-0001-7215-7152</orcidid></search><sort><creationdate>20200807</creationdate><title>Photocatalytic dual decarboxylative alkenylation mediated by triphenylphosphine and sodium iodide</title><author>Wang, Hong-Yu ; Zhong, Long-Jin ; Lv, Gui-Fen ; Li, Yang ; Li, Jin-Heng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c363t-f17a8ad1bac67de3c8b8de3a8614b429eaee3268cc07113f9aee789a18094cd63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Aliphatic compounds</topic><topic>Alkylation</topic><topic>Amino acids</topic><topic>Carboxylic acids</topic><topic>Catalysts</topic><topic>Esters</topic><topic>Iodides</topic><topic>Irradiation</topic><topic>Photocatalysis</topic><topic>Photoredox catalysis</topic><topic>Selectivity</topic><topic>Sodium</topic><topic>Sodium iodide</topic><topic>Styrenes</topic><topic>Transition metals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Hong-Yu</creatorcontrib><creatorcontrib>Zhong, Long-Jin</creatorcontrib><creatorcontrib>Lv, Gui-Fen</creatorcontrib><creatorcontrib>Li, Yang</creatorcontrib><creatorcontrib>Li, Jin-Heng</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Hong-Yu</au><au>Zhong, Long-Jin</au><au>Lv, Gui-Fen</au><au>Li, Yang</au><au>Li, Jin-Heng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photocatalytic dual decarboxylative alkenylation mediated by triphenylphosphine and sodium iodide</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2020-08-07</date><risdate>2020</risdate><volume>18</volume><issue>29</issue><spage>5589</spage><epage>5593</epage><pages>5589-5593</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>An efficient photocatalytic dual decarboxylative alkenylation of α,β-unsaturated carboxylic acids and alkyl
N
-hydroxyphthalimide (NHP) esters mediated by triphenylphosphine and sodium iodide has been developed. This protocol proceeds under 456-nanometer irradiation by visible blue light in the absence of transition metals or organic dye based photoredox catalysts. The reaction is successfully applied to a wide range of redox-active esters derived from aliphatic carboxylic acids (1°, 2° and 3°) and α-amino acids, enabling transformations of diverse α,β-unsaturated carboxylic acids to α,β-alkylated styrenes with high efficiency and excellent selectivity under mild conditions.
A new transition-metal-free photoredox decarboxylative alkylation of α,β-unsaturated carboxylic acids and alkyl
N
-hydroxyphthalimide (NHP) esters by NaI/PPh
3
catalysis has been developed.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>32677630</pmid><doi>10.1039/d0ob01242d</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-6026-4794</orcidid><orcidid>https://orcid.org/0000-0001-7215-7152</orcidid></addata></record> |
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| ispartof | Organic & biomolecular chemistry, 2020-08, Vol.18 (29), p.5589-5593 |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Aliphatic compounds Alkylation Amino acids Carboxylic acids Catalysts Esters Iodides Irradiation Photocatalysis Photoredox catalysis Selectivity Sodium Sodium iodide Styrenes Transition metals |
| title | Photocatalytic dual decarboxylative alkenylation mediated by triphenylphosphine and sodium iodide |
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