An Efficient Catalyst for Pd-Catalyzed Carbonylation of Aryl Arenesulfonates
Aryl carboxylic esters were synthesized by Pd-catalyzed carbonylation of aryl p-fluorobenzenesulfonates or -tosylates. A unique Josiphos ligand was discovered through high-throughput catalyst screening, which was the key for the successful carbonylation of various substrates. This catalyst is effect...
Saved in:
Published in: | Organic letters Vol. 8; no. 22; pp. 5161 - 5164 |
---|---|
Main Authors: | , , , , , , |
Format: | Journal Article |
Language: | English |
Published: |
United States
American Chemical Society
26-10-2006
|
Subjects: | |
Online Access: | Get full text |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
Abstract | Aryl carboxylic esters were synthesized by Pd-catalyzed carbonylation of aryl p-fluorobenzenesulfonates or -tosylates. A unique Josiphos ligand was discovered through high-throughput catalyst screening, which was the key for the successful carbonylation of various substrates. This catalyst is effective and works well for both electron-rich and electron-poor aryl arenesulfonates. Isolated yields of up to 90% were obtained for aryl p-fluorobenzenesulfonates and -tosylates. |
---|---|
AbstractList | Aryl carboxylic esters were synthesized by Pd-catalyzed carbonylation of aryl p-fluorobenzenesulfonates or -tosylates. A unique Josiphos ligand was discovered through high-throughput catalyst screening, which was the key for the successful carbonylation of various substrates. This catalyst is effective and works well for both electron-rich and electron-poor aryl arenesulfonates. Isolated yields of up to 90% were obtained for aryl p-fluorobenzenesulfonates and -tosylates. Aryl carboxylic esters were synthesized by Pd-catalyzed carbonylation of aryl p-fluorobenzenesulfonates or -tosylates. A unique Josiphos ligand was discovered through high-throughput catalyst screening, which was the key for the successful carbonylation of various substrates. This catalyst is effective and works well for both electron-rich and electron-poor aryl arenesulfonates. Isolated yields of up to 90% were obtained for aryl p-fluorobenzenesulfonates and -tosylates. [reaction: see text] |
Author | Shultz, C. Scott Cai, Chaoxian Balsells, Jaume Sidler, Rick R Sun, Yongkui Rivera, Nelo R McWilliams, J. Christopher |
Author_xml | – sequence: 1 givenname: Chaoxian surname: Cai fullname: Cai, Chaoxian – sequence: 2 givenname: Nelo R surname: Rivera fullname: Rivera, Nelo R – sequence: 3 givenname: Jaume surname: Balsells fullname: Balsells, Jaume – sequence: 4 givenname: Rick R surname: Sidler fullname: Sidler, Rick R – sequence: 5 givenname: J. Christopher surname: McWilliams fullname: McWilliams, J. Christopher – sequence: 6 givenname: C. Scott surname: Shultz fullname: Shultz, C. Scott – sequence: 7 givenname: Yongkui surname: Sun fullname: Sun, Yongkui |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/17048868$$D View this record in MEDLINE/PubMed |
BookMark | eNptkD1PwzAQhi0Eoh8w8AdQFgaGwJ3jJvZYVeVDqgQDzJE_UarUrux0CL-eoFRlYbm79-7Rq9M7I-c-eEvIDcIDAsXH0EJJKfCvMzLFBS3yChb0_DSXMCGzlLYAOGzEJZlgBYzzkk_JZumztXONbqzvspXsZNunLnMhZu8mH_W3NcMlquD7VnZN8Flw2TL27VCst-nQuuBlZ9MVuXCyTfb62Ofk82n9sXrJN2_Pr6vlJpcF412upLXIrABaVs4qCsCNLErkhmkqFhoZCKGYRFFpVRqnNHPMMCWQmoJTLObkfvTVMaQUrav3sdnJ2NcI9W8i9SmRgb0d2f1B7az5I48RDMDdCEid6m04RD-8_o_RD8xcaVo |
CitedBy_id | crossref_primary_10_1002_slct_202101394 crossref_primary_10_1002_ange_201400612 crossref_primary_10_1016_j_ccr_2007_02_018 crossref_primary_10_1039_c3ob41011k crossref_primary_10_1002_ajoc_202200554 crossref_primary_10_1080_10241220801967367 crossref_primary_10_1002_anie_200900013 crossref_primary_10_1039_C6RA18388C crossref_primary_10_1246_cl_2007_928 crossref_primary_10_1039_D2QO01621D crossref_primary_10_1021_acs_organomet_8b00468 crossref_primary_10_1021_jo400255m crossref_primary_10_1021_op800069w crossref_primary_10_1002_adsc_201100151 crossref_primary_10_1021_acscatal_2c05159 crossref_primary_10_1021_ol5026519 crossref_primary_10_1016_j_molcata_2015_12_025 crossref_primary_10_1016_j_tetlet_2010_05_104 crossref_primary_10_1002_chin_200708085 crossref_primary_10_1021_ja410883p crossref_primary_10_1002_ange_200900013 crossref_primary_10_1016_j_tetlet_2007_12_134 crossref_primary_10_1021_jo800907e crossref_primary_10_1002_aoc_6073 crossref_primary_10_1002_poc_1569 crossref_primary_10_1016_j_tet_2011_02_077 crossref_primary_10_1039_C7OB01337J crossref_primary_10_1002_adsc_201400710 crossref_primary_10_1002_bkcs_10259 crossref_primary_10_1021_jo801279r crossref_primary_10_1021_ja807167y crossref_primary_10_1021_acs_joc_1c00260 crossref_primary_10_1016_j_tetlet_2020_151660 crossref_primary_10_1039_C5RA00724K crossref_primary_10_1016_j_ica_2015_02_007 crossref_primary_10_1080_00397911_2020_1794657 crossref_primary_10_1016_j_tetlet_2015_08_088 crossref_primary_10_1016_j_tetlet_2015_10_073 crossref_primary_10_1016_j_tet_2021_132444 crossref_primary_10_1021_ja711449e crossref_primary_10_1021_ol200744s crossref_primary_10_1039_C5RA09166G crossref_primary_10_1002_chem_201002273 crossref_primary_10_1021_ja801116s crossref_primary_10_1021_acs_orglett_9b00067 crossref_primary_10_1002_anie_201400612 crossref_primary_10_1016_j_tet_2008_10_024 crossref_primary_10_1021_om800549q crossref_primary_10_1021_acs_orglett_5b01283 crossref_primary_10_1021_acs_joc_1c01290 crossref_primary_10_1002_adsc_200900563 crossref_primary_10_1007_s11696_022_02585_3 crossref_primary_10_1016_j_tet_2008_07_053 crossref_primary_10_1016_j_tet_2010_03_090 crossref_primary_10_1039_D0CY01159B |
Cites_doi | 10.1002/1521-3773(20010803)40:15<2856::AID-ANIE2856>3.0.CO;2-1 10.1021/ja036947t 10.1016/S1381-1169(99)00400-8 10.1021/ja00205a039 10.1016/1381-1169(95)00130-1 10.1016/0304-5102(91)80020-4 10.1021/ol0498287 |
ContentType | Journal Article |
Copyright | Copyright © 2006 American Chemical Society |
Copyright_xml | – notice: Copyright © 2006 American Chemical Society |
DBID | CGR CUY CVF ECM EIF NPM AAYXX CITATION |
DOI | 10.1021/ol062208g |
DatabaseName | Medline MEDLINE MEDLINE (Ovid) MEDLINE MEDLINE PubMed CrossRef |
DatabaseTitle | MEDLINE Medline Complete MEDLINE with Full Text PubMed MEDLINE (Ovid) CrossRef |
DatabaseTitleList | MEDLINE |
Database_xml | – sequence: 1 dbid: ECM name: MEDLINE url: https://search.ebscohost.com/login.aspx?direct=true&db=cmedm&site=ehost-live sourceTypes: Index Database |
DeliveryMethod | fulltext_linktorsrc |
Discipline | Chemistry |
EISSN | 1523-7052 |
EndPage | 5164 |
ExternalDocumentID | 10_1021_ol062208g 17048868 a373605202 |
Genre | Journal Article |
GroupedDBID | - .K2 123 4.4 53G 55A 5VS 7~N AABXI ABFLS ABMVS ABPTK ABUCX ACGFS ACS AEESW AENEX AFEFF ALMA_UNASSIGNED_HOLDINGS AQSVZ BAANH CS3 DU5 DZ EBS ED ED~ F5P GNL IH9 IHE JG JG~ K2 LG6 P2P RNS ROL TN5 UI2 VF5 VG9 W1F X YNT --- -DZ -~X AAHBH ABJNI ABQRX ADHLV AHGAQ CGR CUPRZ CUY CVF ECM EIF GGK NPM AAYXX CITATION |
ID | FETCH-LOGICAL-a348t-baee14e90267feb2008da3618d4c295c14099b4a197cb6dfbc4f4d4b912d38213 |
IEDL.DBID | ACS |
ISSN | 1523-7060 |
IngestDate | Fri Aug 23 00:59:30 EDT 2024 Sat Sep 28 07:50:17 EDT 2024 Thu Feb 04 21:42:56 EST 2021 |
IsPeerReviewed | true |
IsScholarly | true |
Issue | 22 |
Language | English |
LinkModel | DirectLink |
MergedId | FETCHMERGED-LOGICAL-a348t-baee14e90267feb2008da3618d4c295c14099b4a197cb6dfbc4f4d4b912d38213 |
PMID | 17048868 |
PageCount | 4 |
ParticipantIDs | crossref_primary_10_1021_ol062208g pubmed_primary_17048868 acs_journals_10_1021_ol062208g |
ProviderPackageCode | JG~ 55A AABXI GNL VF5 7~N VG9 W1F ACS AEESW AFEFF .K2 ABMVS ABUCX IH9 BAANH AQSVZ ED~ UI2 |
PublicationCentury | 2000 |
PublicationDate | 2006-10-26 |
PublicationDateYYYYMMDD | 2006-10-26 |
PublicationDate_xml | – month: 10 year: 2006 text: 2006-10-26 day: 26 |
PublicationDecade | 2000 |
PublicationPlace | United States |
PublicationPlace_xml | – name: United States |
PublicationTitle | Organic letters |
PublicationTitleAlternate | Org. Lett |
PublicationYear | 2006 |
Publisher | American Chemical Society |
Publisher_xml | – name: American Chemical Society |
References | Beller M. (ol062208gb00002/ol062208gb00002_5) 1995; 104 Nguyen H. N. (ol062208gb00005/ol062208gb00005_1) 2003; 125 Ben-David Y. (ol062208gb00003/ol062208gb00003_4) 1989; 111 Takeuchi R. (ol062208gb00003/ol062208gb00003_3) 1991; 66 Colquhoun H. M. (ol062208gb00002/ol062208gb00002_6) 1991 Albaneze-Walker J. (ol062208gb00003/ol062208gb00003_1) 2004; 6 Magerlein W. (ol062208gb00003/ol062208gb00003_2) 2001; 40 Cacchi S. (ol062208gb00003/ol062208gb00003_6) 1986; 27 Kubota Y. (ol062208gb00004/ol062208gb00004_1) 1998; 183 Tang Z.-Y. (ol062208gb00006/ol062208gb00006_1) 2004; 126 Schoenberg A. (ol062208gb00001/ol062208gb00001_1) 1974; 39 Heck R. F. (ol062208gb00001/ol062208gb00001_2) 1977; 26 Wu X. (ol062208gb00002/ol062208gb00002_1) 2005; 7 Wu G. G. (ol062208gb00002/ol062208gb00002_4) 1999; 1 Dolle R. E. (ol062208gb00003/ol062208gb00003_5) 1987; 904 Ramesh C. (ol062208gb00002/ol062208gb00002_2) 2003; 4 ol062208gb00002/ol062208gb00002_3 |
References_xml | – volume: 26 start-page: 349 year: 1977 ident: ol062208gb00001/ol062208gb00001_2 publication-title: Adv. Catal. contributor: fullname: Heck R. F. – volume: 40 start-page: 2859 year: 2001 ident: ol062208gb00003/ol062208gb00003_2 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/1521-3773(20010803)40:15<2856::AID-ANIE2856>3.0.CO;2-1 contributor: fullname: Magerlein W. – volume: 125 start-page: 11819 year: 2003 ident: ol062208gb00005/ol062208gb00005_1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja036947t contributor: fullname: Nguyen H. N. – volume: 183 start-page: 185 year: 1998 ident: ol062208gb00004/ol062208gb00004_1 publication-title: Synlett contributor: fullname: Kubota Y. – volume: 27 start-page: 3934 year: 1986 ident: ol062208gb00003/ol062208gb00003_6 publication-title: Tetrahedron Lett. contributor: fullname: Cacchi S. – ident: ol062208gb00002/ol062208gb00002_3 doi: 10.1016/S1381-1169(99)00400-8 – volume: 111 start-page: 8744 year: 1989 ident: ol062208gb00003/ol062208gb00003_4 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00205a039 contributor: fullname: Ben-David Y. – volume: 126 start-page: 3059 year: 2004 ident: ol062208gb00006/ol062208gb00006_1 publication-title: J. Am. Chem. Soc. contributor: fullname: Tang Z.-Y. – volume: 4 start-page: 504 year: 2003 ident: ol062208gb00002/ol062208gb00002_2 publication-title: Synthesis contributor: fullname: Ramesh C. – volume: 1 start-page: 747 year: 1999 ident: ol062208gb00002/ol062208gb00002_4 publication-title: Org. Lett. contributor: fullname: Wu G. G. – volume: 104 start-page: 85 year: 1995 ident: ol062208gb00002/ol062208gb00002_5 publication-title: J. Mol. Catal. doi: 10.1016/1381-1169(95)00130-1 contributor: fullname: Beller M. – volume: 7 start-page: 3329 year: 2005 ident: ol062208gb00002/ol062208gb00002_1 publication-title: Org. Lett. contributor: fullname: Wu X. – volume: 66 start-page: 288 year: 1991 ident: ol062208gb00003/ol062208gb00003_3 publication-title: J. Mol. Catal. doi: 10.1016/0304-5102(91)80020-4 contributor: fullname: Takeuchi R. – volume: 6 start-page: 2100 year: 2004 ident: ol062208gb00003/ol062208gb00003_1 publication-title: Org. Lett. doi: 10.1021/ol0498287 contributor: fullname: Albaneze-Walker J. – volume: 39 start-page: 3326 year: 1974 ident: ol062208gb00001/ol062208gb00001_1 publication-title: J. Org. Chem. contributor: fullname: Schoenberg A. – volume-title: Direct Synthesis of Carbonyl Compounds year: 1991 ident: ol062208gb00002/ol062208gb00002_6 contributor: fullname: Colquhoun H. M. – volume: 904 start-page: 905 year: 1987 ident: ol062208gb00003/ol062208gb00003_5 publication-title: J. Chem. Soc., Chem. Commun. contributor: fullname: Dolle R. E. |
SSID | ssj0011529 |
Score | 2.1523042 |
Snippet | Aryl carboxylic esters were synthesized by Pd-catalyzed carbonylation of aryl p-fluorobenzenesulfonates or -tosylates. A unique Josiphos ligand was discovered... |
SourceID | crossref pubmed acs |
SourceType | Aggregation Database Index Database Publisher |
StartPage | 5161 |
SubjectTerms | Arylsulfonates - chemistry Catalysis Combinatorial Chemistry Techniques Esters Hydrocarbons, Fluorinated - chemistry Molecular Structure Palladium Tosyl Compounds - chemistry |
Title | An Efficient Catalyst for Pd-Catalyzed Carbonylation of Aryl Arenesulfonates |
URI | http://dx.doi.org/10.1021/ol062208g https://www.ncbi.nlm.nih.gov/pubmed/17048868 |
Volume | 8 |
hasFullText | 1 |
inHoldings | 1 |
isFullTextHit | |
isPrint | |
link | http://sdu.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwjV3JTsMwEB3RcoAL-1KWKgKuFvXSxD5WoRUHhJAKErcojm0uVYqa9lC-nrHTFiqB4GjFGUXPlt_zTPQG4EayPO4aTolysiDC8Q5ROdfEWIkXLueEMSF1MUweX-Vd39vkXP9SwWf0djzqxIx15FsDNlmCCsHrn3S4KhUgAalgiso48VYwS_ug76966imqNepZE5GBTAa7__qMPdhZaMWoVy_uPmzY8gC20mWLtkN46JVRP3hAIHVEqc_EzKtphDo0ejKkHn9Yg08m2v-BHlYhGjsMOfdx_Tk3GzmfQLfVEbwM-s_pPVm0RyA5F3JKdG4tFVb5HlIOL8jI5ibnMZVGFEx1C29lpbTIqUoKHRunC4HQC60oM1wyyo-hWY5LewoR06gcbFckSqKiKmLNnDLa4ZBx78vUgjbily22d5WFyjWj2QqUFlwtoc3ea5uMnyad1KB_TUn8ARLLs7_in8N2yH0gabD4AprTycxeQqMys3bYDZ_E6KsT |
link.rule.ids | 315,782,786,2769,27085,27933,27934,56747,56797 |
linkProvider | American Chemical Society |
linkToHtml | http://sdu.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV1LSwMxEA62HurF96M-6iJeg90km02OpbZUrEVoBW_LZpN4KVvptof6651k-7AgiMew2SHMhHxfZna_QehekJRHmoZYWpFhZmkTy5QqrI2AC5e1TGufuhjGg3fx2FnL5Lh_YWARBVgqfBF_oy4QPkzGTU5IU3xU0G7EgQQ7GtQerisGgEPSa6MSip0izEpF6OerDoGyYguBtrikx5TuwX9Wc4j2l8wxaJWhPkI7Jj9GtfaqYdsJ6rfyoOMVIQBIgrbLyyyKWQCsNHjVuBx_GQ1Ppsp9j-5jEkwsmFw4u-7Um4-tS6eb4hS9dTujdg8vmyXglDIxwyo1JmRGuo5SFq7LgO06pTwUmmVERpkTtpKKpaGMM8W1VRmDQDAlQ6KpICE9Q9V8kpsLFBAFPMJELJYC-FXGFbFSKwtDQp1KUx01wCfJcrMXia9jkzBZO6WO7lYeTj5L0YzfJp2Xvt9Mid1xwsXlX_ZvUa03eukn_afB8xXa81kRgBPCr1F1Np2bG1Qp9LzhN8g3wnyzgA |
linkToPdf | http://sdu.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwlV1bS8MwFA5ugvri_TIvs4iv0eXSNHkcu6A4xmAKvpWmSXwZ3Vi3h_nrTdJ2OhDEx9D0EM5J851L-h0A7jlOWKgIgsLwFFJDWlAkREKluQ24jKFK-dTFOBq-827P0eQ8VP_C2EXkVlLui_juq54pUzIMoMfppMUwbvGPGtgOWSRcsNXujNdVA4tFwvOjYgIdK0zFJPTzVYdCab6BQhv-pMeV_sF_V3QI9ksPMmgXJj8CWzo7BrudqnHbCRi0s6DnmSEsoAQdl59Z5YvAeqfBSMFi_KmVfTKX7l66t00wNVbkysl1p99yYlxaXeen4K3fe-08wbJpAkwI5QsoE60R1cJ1ljI2bLYYrxLCEFc0xSJMHcGVkDRBIkolU0am1BqESoGwIhwjcgbq2TTTFyDA0voTOqSR4NbPSpnERihp7BATx9bUAE2rl7jc9Hns69kYxWulNMBdpeV4VpBn_DbpvND_95TIHSuMX_4l_xbsjLr9ePA8fLkCez45YlEFs2tQX8yX-gbUcrVs-j3yBe4KtgM |
openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=An+Efficient+Catalyst+for+Pd-Catalyzed+Carbonylation+of+Aryl+Arenesulfonates&rft.jtitle=Organic+letters&rft.au=Cai%2C+Chaoxian&rft.au=Rivera%2C+Nelo+R.&rft.au=Balsells%2C+Jaume&rft.au=Sidler%2C+Rick+R.&rft.date=2006-10-26&rft.issn=1523-7060&rft.eissn=1523-7052&rft.volume=8&rft.issue=22&rft.spage=5161&rft.epage=5164&rft_id=info:doi/10.1021%2Fol062208g&rft.externalDBID=n%2Fa&rft.externalDocID=10_1021_ol062208g |
thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1523-7060&client=summon |
thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1523-7060&client=summon |
thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1523-7060&client=summon |