Rational Synthesis of meso- or β- Fluoroalkylporphyrin Derivatives via Halo-fluoroalkylporphyrin Precursors:  Electronic and Steric Effects on Regioselective Electrophilic Substitution in 5-Fluoroalkyl-10,20-diarylporphyrins

[reaction: see text] Electrophilic nitration, formylation or bromination of metalated 5-fluoroalkyl-10,20-diphenylporphyrin (fluoroalkyl = CF3, ClCF2CF2, n-C6F13) proceeded with high regioselectivity, exclusively affording corresponding meso-substituted porphyrins, while the iodination reaction main...

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Published in:Journal of organic chemistry 2006-01, Vol.71 (2), p.527-536
Main Authors: JIN, Li-Mei, CHEN, Liang, YIN, Juan-Juan, ZHOU, Jin-Ming, GUO, Can-Cheng, CHEN, Qing-Yun
Format: Article
Language:English
Subjects:
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
Prostaglandins
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container_title Journal of organic chemistry
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creator JIN, Li-Mei
CHEN, Liang
YIN, Juan-Juan
ZHOU, Jin-Ming
GUO, Can-Cheng
CHEN, Qing-Yun
description [reaction: see text] Electrophilic nitration, formylation or bromination of metalated 5-fluoroalkyl-10,20-diphenylporphyrin (fluoroalkyl = CF3, ClCF2CF2, n-C6F13) proceeded with high regioselectivity, exclusively affording corresponding meso-substituted porphyrins, while the iodination reaction mainly took place at the adjacent beta site giving 2-iodo-10-fluoroalkyl-5,15-diphenylporphyrin. Suzuki, Sonogashira, and trifluoromethylation reactions of the obtained 5-bromo-15-fluoroalkyl-10,20-diphenylporphyrins or 2-iodo-10-fluoroalkyl-5,15-diphenylporphyrins could perform smoothly to give the corresponding various meso- or beta-functionalized fluoroalkylated porphyrin derivatives. Accordingly, two meso-to-meso butadiyne-bridged bisporphyrin dimers and two beta-to-beta butadiyne-linked dimeric porphyrins were prepared by the coupling reactions of 5-ethynyl-15-fluoroalkyl-10,20-diphenylporphyrins and 2-ethynyl-10-fluoroalkyl-5,15-diphenylporphyrins, respectively.
doi_str_mv 10.1021/jo051672g
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Suzuki, Sonogashira, and trifluoromethylation reactions of the obtained 5-bromo-15-fluoroalkyl-10,20-diphenylporphyrins or 2-iodo-10-fluoroalkyl-5,15-diphenylporphyrins could perform smoothly to give the corresponding various meso- or beta-functionalized fluoroalkylated porphyrin derivatives. Accordingly, two meso-to-meso butadiyne-bridged bisporphyrin dimers and two beta-to-beta butadiyne-linked dimeric porphyrins were prepared by the coupling reactions of 5-ethynyl-15-fluoroalkyl-10,20-diphenylporphyrins and 2-ethynyl-10-fluoroalkyl-5,15-diphenylporphyrins, respectively.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo051672g</identifier><identifier>PMID: 16408960</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids ; Chemistry ; Exact sciences and technology ; Organic chemistry ; Preparations and properties ; Prostaglandins</subject><ispartof>Journal of organic chemistry, 2006-01, Vol.71 (2), p.527-536</ispartof><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&amp;idt=17700504$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16408960$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>JIN, Li-Mei</creatorcontrib><creatorcontrib>CHEN, Liang</creatorcontrib><creatorcontrib>YIN, Juan-Juan</creatorcontrib><creatorcontrib>ZHOU, Jin-Ming</creatorcontrib><creatorcontrib>GUO, Can-Cheng</creatorcontrib><creatorcontrib>CHEN, Qing-Yun</creatorcontrib><title>Rational Synthesis of meso- or β- Fluoroalkylporphyrin Derivatives via Halo-fluoroalkylporphyrin Precursors:  Electronic and Steric Effects on Regioselective Electrophilic Substitution in 5-Fluoroalkyl-10,20-diarylporphyrins</title><title>Journal of organic chemistry</title><addtitle>J. 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Accordingly, two meso-to-meso butadiyne-bridged bisporphyrin dimers and two beta-to-beta butadiyne-linked dimeric porphyrins were prepared by the coupling reactions of 5-ethynyl-15-fluoroalkyl-10,20-diphenylporphyrins and 2-ethynyl-10-fluoroalkyl-5,15-diphenylporphyrins, respectively.</description><subject>Alicyclic compounds, terpenoids, prostaglandins, steroids</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Prostaglandins</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><recordid>eNpt0c9uFCEABnBiNHZtPfgChoueRPnPjDezbq1JGzfd1euEmWG6tOwwArPp3nr1dXwQH6J9EWm61R7KhQR-fHwEAF4R_J5gSj6ceyyIVPTsCZgQQTGSJeZPwQRjShGjku2BFzGe4zyEEM_BHpEcF6XEE3BzqpP1vXZwse3TykQboe_g2kSPoA_wz28ED93og9fuYusGH4bVNtgefjbBbvLZjYlwYzU80s6j7jE5D6YZQ_Qhfry--gVnzjQp-N42UPctXKQc1MBZ1-XlfHcPT82Z9dHcspx-74eVddktxjomm8bb0jCHC_SgHSL4XX59a3V4UCAegGeddtG83M374PvhbDk9QsffvnydfjpGliqVEJctN6rmLaemNpwwTLVoJRaqkLWipShwwWihCae6bhUphSxLzWUWXds1DdsHb-9yh-B_jiamam1jY5zTvfFjrBSWqlCMZfh6B8d6bdpqCHadK1f335LBmx3QsdGuC7pvbPzvlMo_iXl26M7ZmMzlv30dLiqpmBLVcr6oTqZzTqbLH9UJ-wtEcrIj</recordid><startdate>20060120</startdate><enddate>20060120</enddate><creator>JIN, Li-Mei</creator><creator>CHEN, Liang</creator><creator>YIN, Juan-Juan</creator><creator>ZHOU, Jin-Ming</creator><creator>GUO, Can-Cheng</creator><creator>CHEN, Qing-Yun</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20060120</creationdate><title>Rational Synthesis of meso- or β- Fluoroalkylporphyrin Derivatives via Halo-fluoroalkylporphyrin Precursors:  Electronic and Steric Effects on Regioselective Electrophilic Substitution in 5-Fluoroalkyl-10,20-diarylporphyrins</title><author>JIN, Li-Mei ; CHEN, Liang ; YIN, Juan-Juan ; ZHOU, Jin-Ming ; GUO, Can-Cheng ; CHEN, Qing-Yun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-i277t-46d4e7b4d42ebe41302a5d605786b7295808328a142abd7195699a46605fdfcc3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Alicyclic compounds, terpenoids, prostaglandins, steroids</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Prostaglandins</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>JIN, Li-Mei</creatorcontrib><creatorcontrib>CHEN, Liang</creatorcontrib><creatorcontrib>YIN, Juan-Juan</creatorcontrib><creatorcontrib>ZHOU, Jin-Ming</creatorcontrib><creatorcontrib>GUO, Can-Cheng</creatorcontrib><creatorcontrib>CHEN, Qing-Yun</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>JIN, Li-Mei</au><au>CHEN, Liang</au><au>YIN, Juan-Juan</au><au>ZHOU, Jin-Ming</au><au>GUO, Can-Cheng</au><au>CHEN, Qing-Yun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Rational Synthesis of meso- or β- Fluoroalkylporphyrin Derivatives via Halo-fluoroalkylporphyrin Precursors:  Electronic and Steric Effects on Regioselective Electrophilic Substitution in 5-Fluoroalkyl-10,20-diarylporphyrins</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2006-01-20</date><risdate>2006</risdate><volume>71</volume><issue>2</issue><spage>527</spage><epage>536</epage><pages>527-536</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>[reaction: see text] Electrophilic nitration, formylation or bromination of metalated 5-fluoroalkyl-10,20-diphenylporphyrin (fluoroalkyl = CF3, ClCF2CF2, n-C6F13) proceeded with high regioselectivity, exclusively affording corresponding meso-substituted porphyrins, while the iodination reaction mainly took place at the adjacent beta site giving 2-iodo-10-fluoroalkyl-5,15-diphenylporphyrin. Suzuki, Sonogashira, and trifluoromethylation reactions of the obtained 5-bromo-15-fluoroalkyl-10,20-diphenylporphyrins or 2-iodo-10-fluoroalkyl-5,15-diphenylporphyrins could perform smoothly to give the corresponding various meso- or beta-functionalized fluoroalkylated porphyrin derivatives. Accordingly, two meso-to-meso butadiyne-bridged bisporphyrin dimers and two beta-to-beta butadiyne-linked dimeric porphyrins were prepared by the coupling reactions of 5-ethynyl-15-fluoroalkyl-10,20-diphenylporphyrins and 2-ethynyl-10-fluoroalkyl-5,15-diphenylporphyrins, respectively.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>16408960</pmid><doi>10.1021/jo051672g</doi><tpages>10</tpages></addata></record>
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subjects Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
Prostaglandins
title Rational Synthesis of meso- or β- Fluoroalkylporphyrin Derivatives via Halo-fluoroalkylporphyrin Precursors:  Electronic and Steric Effects on Regioselective Electrophilic Substitution in 5-Fluoroalkyl-10,20-diarylporphyrins
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