Metal-free naphthannulation reactions of yne-allenone esters for accessing polycyclic aromatic hydrocarbons

The first metal-free base-promoted naphthannulation reactions of yne-allenone esters were established for the direct assembly of a wide range of polycyclic aromatic hydrocarbons with generally good yields. The naphthannulation reaction of yne-allenone esters with β-ketonitriles provided new phenanth...

Full description

Saved in:
Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2018, Vol.54 (74), p.1415-1418
Main Authors: Sha, Hong-Kai, Xu, Ting, Liu, Feng, Tang, Bu-Zheng, Hao, Wen-Juan, Tu, Shu-Jiang, Jiang, Bo
Format: Article
Language:English
Subjects:
Carboxylates
Chemical reactions
Cycloaddition
Esters
Organic chemistry
Phenanthrene
Polycyclic aromatic hydrocarbons
Reagents
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c403t-434bc3de8fe5e8ea689646e1d9d589e4bbde753d4226b928d113635ff1f6a8513
cites cdi_FETCH-LOGICAL-c403t-434bc3de8fe5e8ea689646e1d9d589e4bbde753d4226b928d113635ff1f6a8513
container_end_page 1418
container_issue 74
container_start_page 1415
container_title Chemical communications (Cambridge, England)
container_volume 54
creator Sha, Hong-Kai
Xu, Ting
Liu, Feng
Tang, Bu-Zheng
Hao, Wen-Juan
Tu, Shu-Jiang
Jiang, Bo
description The first metal-free base-promoted naphthannulation reactions of yne-allenone esters were established for the direct assembly of a wide range of polycyclic aromatic hydrocarbons with generally good yields. The naphthannulation reaction of yne-allenone esters with β-ketonitriles provided new phenanthrene-1-carboxylates via a base-mediated [2+2] cycloaddition/ring expansion sequence, whereas hitherto unreported tetracyclic tetrahydrotetraphene-7-carboxylates were obtained with good yield via a sequential double annulation cascade of yne-allenone esters with dimedone as a diphilic reagent. The first metal-free base-promoted naphthannulation reactions of yne-allenone esters were developed for the direct assembly of a wide range of polycyclic aromatic hydrocarbons with generally good yields.
doi_str_mv 10.1039/c8cc05018j
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1039_C8CC05018J</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2103509393</sourcerecordid><originalsourceid>FETCH-LOGICAL-c403t-434bc3de8fe5e8ea689646e1d9d589e4bbde753d4226b928d113635ff1f6a8513</originalsourceid><addsrcrecordid>eNpdkU1r3DAQhkVoySabXHJPEOQSAm4lS_JKx2DyVbbk0kBvRpZHXW-00layD_730XbTBDIMzMA8vMzMi9AZJd8oYeq7kcYQQahcH6AjyipeCC5_f9n1QhULxsUMHae0JjmokIdoxgiplKjKI_TyEwbtChsBsNfb1bDS3o9OD33wOII2uybhYPHkodDOgQ8eMKQBYsI2RKyNgZR6_wdvg5vMZFxvsI5hkzUMXk1dDEbHNqucoK9WuwSnb3WOnu9uf9UPxfLp_rG-WRaGEzYUnPHWsA6kBQESdCVVxSugneqEVMDbtoOFYB0vy6pVpexovpkJa6mttBSUzdHVXncbw98xr9ps-mTAOe0hjKkpicypJNuhl5_QdRijz9s1Zf6tIIoplqnrPWViSCmCbbax3-g4NZQ0OwuaWtb1Pwt-ZPjiTXJsN9C9o_9_noHzPRCTeZ9-eMheAU5BjJM</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2103509393</pqid></control><display><type>article</type><title>Metal-free naphthannulation reactions of yne-allenone esters for accessing polycyclic aromatic hydrocarbons</title><source>Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list)</source><creator>Sha, Hong-Kai ; Xu, Ting ; Liu, Feng ; Tang, Bu-Zheng ; Hao, Wen-Juan ; Tu, Shu-Jiang ; Jiang, Bo</creator><creatorcontrib>Sha, Hong-Kai ; Xu, Ting ; Liu, Feng ; Tang, Bu-Zheng ; Hao, Wen-Juan ; Tu, Shu-Jiang ; Jiang, Bo</creatorcontrib><description>The first metal-free base-promoted naphthannulation reactions of yne-allenone esters were established for the direct assembly of a wide range of polycyclic aromatic hydrocarbons with generally good yields. The naphthannulation reaction of yne-allenone esters with β-ketonitriles provided new phenanthrene-1-carboxylates via a base-mediated [2+2] cycloaddition/ring expansion sequence, whereas hitherto unreported tetracyclic tetrahydrotetraphene-7-carboxylates were obtained with good yield via a sequential double annulation cascade of yne-allenone esters with dimedone as a diphilic reagent. The first metal-free base-promoted naphthannulation reactions of yne-allenone esters were developed for the direct assembly of a wide range of polycyclic aromatic hydrocarbons with generally good yields.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/c8cc05018j</identifier><identifier>PMID: 30069562</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Carboxylates ; Chemical reactions ; Cycloaddition ; Esters ; Organic chemistry ; Phenanthrene ; Polycyclic aromatic hydrocarbons ; Reagents</subject><ispartof>Chemical communications (Cambridge, England), 2018, Vol.54 (74), p.1415-1418</ispartof><rights>Copyright Royal Society of Chemistry 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c403t-434bc3de8fe5e8ea689646e1d9d589e4bbde753d4226b928d113635ff1f6a8513</citedby><cites>FETCH-LOGICAL-c403t-434bc3de8fe5e8ea689646e1d9d589e4bbde753d4226b928d113635ff1f6a8513</cites><orcidid>0000-0003-3732-233X ; 0000-0003-3878-515X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,4024,27923,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30069562$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sha, Hong-Kai</creatorcontrib><creatorcontrib>Xu, Ting</creatorcontrib><creatorcontrib>Liu, Feng</creatorcontrib><creatorcontrib>Tang, Bu-Zheng</creatorcontrib><creatorcontrib>Hao, Wen-Juan</creatorcontrib><creatorcontrib>Tu, Shu-Jiang</creatorcontrib><creatorcontrib>Jiang, Bo</creatorcontrib><title>Metal-free naphthannulation reactions of yne-allenone esters for accessing polycyclic aromatic hydrocarbons</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>The first metal-free base-promoted naphthannulation reactions of yne-allenone esters were established for the direct assembly of a wide range of polycyclic aromatic hydrocarbons with generally good yields. The naphthannulation reaction of yne-allenone esters with β-ketonitriles provided new phenanthrene-1-carboxylates via a base-mediated [2+2] cycloaddition/ring expansion sequence, whereas hitherto unreported tetracyclic tetrahydrotetraphene-7-carboxylates were obtained with good yield via a sequential double annulation cascade of yne-allenone esters with dimedone as a diphilic reagent. The first metal-free base-promoted naphthannulation reactions of yne-allenone esters were developed for the direct assembly of a wide range of polycyclic aromatic hydrocarbons with generally good yields.</description><subject>Carboxylates</subject><subject>Chemical reactions</subject><subject>Cycloaddition</subject><subject>Esters</subject><subject>Organic chemistry</subject><subject>Phenanthrene</subject><subject>Polycyclic aromatic hydrocarbons</subject><subject>Reagents</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpdkU1r3DAQhkVoySabXHJPEOQSAm4lS_JKx2DyVbbk0kBvRpZHXW-00layD_730XbTBDIMzMA8vMzMi9AZJd8oYeq7kcYQQahcH6AjyipeCC5_f9n1QhULxsUMHae0JjmokIdoxgiplKjKI_TyEwbtChsBsNfb1bDS3o9OD33wOII2uybhYPHkodDOgQ8eMKQBYsI2RKyNgZR6_wdvg5vMZFxvsI5hkzUMXk1dDEbHNqucoK9WuwSnb3WOnu9uf9UPxfLp_rG-WRaGEzYUnPHWsA6kBQESdCVVxSugneqEVMDbtoOFYB0vy6pVpexovpkJa6mttBSUzdHVXncbw98xr9ps-mTAOe0hjKkpicypJNuhl5_QdRijz9s1Zf6tIIoplqnrPWViSCmCbbax3-g4NZQ0OwuaWtb1Pwt-ZPjiTXJsN9C9o_9_noHzPRCTeZ9-eMheAU5BjJM</recordid><startdate>2018</startdate><enddate>2018</enddate><creator>Sha, Hong-Kai</creator><creator>Xu, Ting</creator><creator>Liu, Feng</creator><creator>Tang, Bu-Zheng</creator><creator>Hao, Wen-Juan</creator><creator>Tu, Shu-Jiang</creator><creator>Jiang, Bo</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-3732-233X</orcidid><orcidid>https://orcid.org/0000-0003-3878-515X</orcidid></search><sort><creationdate>2018</creationdate><title>Metal-free naphthannulation reactions of yne-allenone esters for accessing polycyclic aromatic hydrocarbons</title><author>Sha, Hong-Kai ; Xu, Ting ; Liu, Feng ; Tang, Bu-Zheng ; Hao, Wen-Juan ; Tu, Shu-Jiang ; Jiang, Bo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c403t-434bc3de8fe5e8ea689646e1d9d589e4bbde753d4226b928d113635ff1f6a8513</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Carboxylates</topic><topic>Chemical reactions</topic><topic>Cycloaddition</topic><topic>Esters</topic><topic>Organic chemistry</topic><topic>Phenanthrene</topic><topic>Polycyclic aromatic hydrocarbons</topic><topic>Reagents</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sha, Hong-Kai</creatorcontrib><creatorcontrib>Xu, Ting</creatorcontrib><creatorcontrib>Liu, Feng</creatorcontrib><creatorcontrib>Tang, Bu-Zheng</creatorcontrib><creatorcontrib>Hao, Wen-Juan</creatorcontrib><creatorcontrib>Tu, Shu-Jiang</creatorcontrib><creatorcontrib>Jiang, Bo</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sha, Hong-Kai</au><au>Xu, Ting</au><au>Liu, Feng</au><au>Tang, Bu-Zheng</au><au>Hao, Wen-Juan</au><au>Tu, Shu-Jiang</au><au>Jiang, Bo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Metal-free naphthannulation reactions of yne-allenone esters for accessing polycyclic aromatic hydrocarbons</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2018</date><risdate>2018</risdate><volume>54</volume><issue>74</issue><spage>1415</spage><epage>1418</epage><pages>1415-1418</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>The first metal-free base-promoted naphthannulation reactions of yne-allenone esters were established for the direct assembly of a wide range of polycyclic aromatic hydrocarbons with generally good yields. The naphthannulation reaction of yne-allenone esters with β-ketonitriles provided new phenanthrene-1-carboxylates via a base-mediated [2+2] cycloaddition/ring expansion sequence, whereas hitherto unreported tetracyclic tetrahydrotetraphene-7-carboxylates were obtained with good yield via a sequential double annulation cascade of yne-allenone esters with dimedone as a diphilic reagent. The first metal-free base-promoted naphthannulation reactions of yne-allenone esters were developed for the direct assembly of a wide range of polycyclic aromatic hydrocarbons with generally good yields.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>30069562</pmid><doi>10.1039/c8cc05018j</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0003-3732-233X</orcidid><orcidid>https://orcid.org/0000-0003-3878-515X</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1359-7345
ispartof Chemical communications (Cambridge, England), 2018, Vol.54 (74), p.1415-1418
issn 1359-7345
1364-548X
language eng
recordid cdi_crossref_primary_10_1039_C8CC05018J
source Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list)
subjects Carboxylates
Chemical reactions
Cycloaddition
Esters
Organic chemistry
Phenanthrene
Polycyclic aromatic hydrocarbons
Reagents
title Metal-free naphthannulation reactions of yne-allenone esters for accessing polycyclic aromatic hydrocarbons
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-25T20%3A27%3A48IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Metal-free%20naphthannulation%20reactions%20of%20yne-allenone%20esters%20for%20accessing%20polycyclic%20aromatic%20hydrocarbons&rft.jtitle=Chemical%20communications%20(Cambridge,%20England)&rft.au=Sha,%20Hong-Kai&rft.date=2018&rft.volume=54&rft.issue=74&rft.spage=1415&rft.epage=1418&rft.pages=1415-1418&rft.issn=1359-7345&rft.eissn=1364-548X&rft_id=info:doi/10.1039/c8cc05018j&rft_dat=%3Cproquest_cross%3E2103509393%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c403t-434bc3de8fe5e8ea689646e1d9d589e4bbde753d4226b928d113635ff1f6a8513%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2103509393&rft_id=info:pmid/30069562&rfr_iscdi=true