Biaryl Synthesis via Direct Arylation: Establishment of an Efficient Catalyst for Intramolecular Processes
In this Communication, we describe direct arylation reactions with improved scope and catalyst activity for the intramolecular formation of biaryl compounds. This was achieved through the establishment of a highly active and robust catalyst system and the subsequent development of a novel phosphine...
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Published in | Journal of the American Chemical Society Vol. 126; no. 30; pp. 9186 - 9187 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
04.08.2004
Amer Chemical Soc |
Subjects | |
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Abstract | In this Communication, we describe direct arylation reactions with improved scope and catalyst activity for the intramolecular formation of biaryl compounds. This was achieved through the establishment of a highly active and robust catalyst system and the subsequent development of a novel phosphine ligand 27. The enhanced catalytic activity extends these transformations to include previously unreactive and poorly reactive substrates, and allows for very low catalyst loadings to be employedas little as 0.1 mol %. |
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AbstractList | In this Communication, we describe direct arylation reactions with improved scope and catalyst activity for the intramolecular formation of biaryl compounds. This was achieved through the establishment of a highly active and robust catalyst system and the subsequent development of a novel phosphine ligand 27. The enhanced catalytic activity extends these transformations to include previously unreactive and poorly reactive substrates, and allows for very low catalyst loadings to be employed-as little as 0.1 mol %. In this Communication, we describe direct arylation reactions with improved scope and catalyst activity for the intramolecular formation of biaryl compounds. This was achieved through the establishment of a highly active and robust catalyst system and the subsequent development of a novel phosphine ligand 27. The enhanced catalytic activity extends these transformations to include previously unreactive and poorly reactive substrates, and allows for very low catalyst loadings to be employedas little as 0.1 mol %. |
Author | Campeau, Louis-Charles Leblanc, Melissa Parisien, Mathieu Fagnou, Keith |
Author_xml | – sequence: 1 givenname: Louis-Charles surname: Campeau fullname: Campeau, Louis-Charles – sequence: 2 givenname: Mathieu surname: Parisien fullname: Parisien, Mathieu – sequence: 3 givenname: Melissa surname: Leblanc fullname: Leblanc, Melissa – sequence: 4 givenname: Keith surname: Fagnou fullname: Fagnou, Keith |
BackLink | http://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15990172$$DView record in Pascal Francis https://www.ncbi.nlm.nih.gov/pubmed/15281800$$D View this record in MEDLINE/PubMed |
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Cites_doi | 10.1021/ja0259279 10.1021/ja047980y 10.1021/cr000664r 10.1021/ja037546g 10.1021/ol049866q 10.1016/j.tetlet.2003.09.151 10.1021/ja029273f 10.1021/ol027266q 10.1021/ja034848+ 10.1002/anie.200301753 10.1016/j.tetlet.2003.09.026 10.1021/jo990568u 10.1016/0022-328X(92)80031-R 10.1002/anie.200390037 10.1002/(SICI)1521-3773(19990503)38:9<1229::AID-ANIE1229>3.0.CO;2-B 10.1016/S0040-4020(01)91149-4 10.1021/jo961876k 10.1016/S0040-4039(99)02235-2 10.1002/1521-3765(20010601)7:11<2341::AID-CHEM23410>3.0.CO;2-S |
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Keywords | FUNCTIONALIZATION MIGRATION ABSOLUTE ANTIBIOTICS PHENOLS ARYL HALIDES FUSED POLYCYCLES C-H ACTIVATION BROMIDES CYCLIZATION Intramolecular reaction Platinoid Compounds Arylation Catalytic reaction Catalyst selectivity Transition metal Compounds Complex catalyst Experimental study Palladium compound Catalyst activity |
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References | MATSUMOTO, T (WOS:A1992HQ81400069) 1992; 114 Satoh, T (WOS:A1997XX18100020) 1997; 36 Bringmann, G (WOS:000085335200014) 2000; 65 Hassan, J (WOS:000175550000003) 2002; 102 Campo, MA (WOS:000185711100026) 2003; 125 Okazawa, T (WOS:000175521200017) 2002; 124 AMES, DE (WOS:A1984SX96100038) 1984; 40 CATELLANI, M (WOS:A1992HJ16400015) 1992; 425 Bringmann, G (WOS:000086348400021) 2000; 65 DIEDERICH F (WOS:000222950900019.8) 1998 Futagami, S (WOS:000085357000019) 2000; 41 Hennings, DD (WOS:A1997WC12200002) 1997; 62 Harayama, T (WOS:000071491900011) 1997; 46 Harris, MC (WOS:000081997500042) 1999; 64 Miura, M (WOS:000221040600004) 2004; 43 Martin-Matute, B (WOS:000169209900008) 2001; 7 Kakiuchi, F (WOS:000181088000009) 2003; 125 Hennessy, EJ (WOS:000185784700012) 2003; 125 Cuny, GD (WOS:000185941000024) 2003; 44 Kametani, Y (WOS:000086555200033) 2000; 41 Qabaja, G (WOS:000165199000052) 2000; 65 Sezen, B (WOS:000182682700014) 2003; 125 Kitamura, M (WOS:000080170100010) 1999; 38 Oi, S (WOS:000186474400007) 2003; 44 RICE, JE (WOS:A1995TH61000064) 1995; 60 HOSOYA, T (WOS:A1994MW99000023) 1994; 116 Huang, QH (WOS:000222120900024) 2004; 126 Park, CH (WOS:000220508600023) 2004; 6 ZOLLINGER H (WOS:000222950900019.32) 1964; 2 Oi, S (WOS:000077083700009) 1998 Glover, B (WOS:000180766400018) 2003; 5 Bedford, RB (WOS:000180458100024) 2003; 42 Zollinger H. (ja049017yb00017/ja049017yb00017_1) 1964; 2 For (ja049017yb00002/ja049017yb00002_1) 2003; 125 Martin-Matute B. (ja049017yb00015/ja049017yb00015_1) 2001; 7 Ames (ja049017yb00008/ja049017yb00008_1) 1984; 40 With (ja049017yb00004/ja049017yb00004_1) 1999; 38 For (ja049017yb00001/ja049017yb00001_1) 2002; 102 Catellani M. (ja049017yb00015/ja049017yb00015_2) 1992; 425 Harris M. C. (ja049017yb00010/ja049017yb00010_1) 1999; 64 For (ja049017yb00012/ja049017yb00012_1) 2004; 43 For (ja049017yb00016/ja049017yb00016_1) 2003; 125 Hennings D. D. (ja049017yb00007/ja049017yb00007_1) 1997; 62 Current (ja049017yb00003/ja049017yb00003_1) 2003; 42 After (ja049017yb00006/ja049017yb00006_1) 2004; 126 Futagami S. (ja049017yb00005/ja049017yb00005_1) 2000; 41 |
References_xml | – volume: 124 start-page: 5286 year: 2002 ident: WOS:000175521200017 article-title: Palladium-catalyzed multiple arylation of thiophenes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0259279 contributor: fullname: Okazawa, T – year: 1998 ident: WOS:000222950900019.8 publication-title: METAL CATALYZED CROS contributor: fullname: DIEDERICH F – volume: 126 start-page: 7460 year: 2004 ident: WOS:000222120900024 article-title: Pd-catalyzed alkyl to aryl migration and cyclization: An efficient synthesis of fused polycycles via multiple C-H activation publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja047980y contributor: fullname: Huang, QH – volume: 125 start-page: 11506 year: 2003 ident: WOS:000185711100026 article-title: 1,4-Palladium migration via C-H activation, followed by arylation: Synthesis of fused polycycles publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Campo, MA – volume: 40 start-page: 1919 year: 1984 ident: WOS:A1984SX96100038 article-title: PALLADIUM-CATALYZED CYCLIZATION OF 2-SUBSTITUTED HALOGENOARENES BY DEHYDROHALOGENATION publication-title: TETRAHEDRON contributor: fullname: AMES, DE – volume: 2 start-page: 162 year: 1964 ident: WOS:000222950900019.32 publication-title: ADV PHYS ORG CHEM contributor: fullname: ZOLLINGER H – volume: 64 start-page: 6019 year: 1999 ident: WOS:000081997500042 article-title: Sequential N-arylation of primary amines as a route to alkyldiarylamines publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Harris, MC – volume: 41 start-page: 2655 year: 2000 ident: WOS:000086555200033 article-title: Regioselective arylation of benzanilides with aryl triflates or bromides under palladium catalysis publication-title: TETRAHEDRON LETTERS contributor: fullname: Kametani, Y – volume: 65 start-page: 2069 year: 2000 ident: WOS:000086348400021 article-title: First atropo-divergent total synthesis of the antimalarial korupensamines A and B by the "lactone method" publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Bringmann, G – volume: 102 start-page: 1359 year: 2002 ident: WOS:000175550000003 article-title: Aryl-aryl bond formation one century after the discovery of the Ullmann reaction publication-title: CHEMICAL REVIEWS doi: 10.1021/cr000664r contributor: fullname: Hassan, J – volume: 41 start-page: 1063 year: 2000 ident: WOS:000085357000019 article-title: Total synthesis of ravidomycin: revision of absolute and relative stereochemistry publication-title: TETRAHEDRON LETTERS contributor: fullname: Futagami, S – volume: 425 start-page: 151 year: 1992 ident: WOS:A1992HJ16400015 article-title: PALLADACYCLE FORMATION BY ELECTROPHILIC AROMATIC-SUBSTITUTION, AS MONITORED BY H-1-NMR SPECTROSCOPY publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY contributor: fullname: CATELLANI, M – volume: 125 start-page: 12084 year: 2003 ident: WOS:000185784700012 article-title: Synthesis of substituted oxindoles from alpha-chloroacetanilides via palladium-catalyzed C-H functionalization publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja037546g contributor: fullname: Hennessy, EJ – volume: 62 start-page: 2 year: 1997 ident: WOS:A1997WC12200002 article-title: Anion-accelerated palladium-catalyzed intramolecular coupling of phenols with aryl halides publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Hennings, DD – volume: 116 start-page: 1004 year: 1994 ident: WOS:A1994MW99000023 article-title: TOTAL SYNTHESIS OF THE GILVOCARCINS publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: HOSOYA, T – volume: 6 start-page: 1159 year: 2004 ident: WOS:000220508600023 article-title: Palladium-catalyzed arylation and heteroarylation of indolizines publication-title: ORGANIC LETTERS doi: 10.1021/ol049866q contributor: fullname: Park, CH – volume: 65 start-page: 722 year: 2000 ident: WOS:000085335200014 article-title: Atropisomerization barriers of configurationally unstable biaryl compounds, useful substrates for atroposelective conversions to axially chiral biaryls publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Bringmann, G – volume: 46 start-page: 61 year: 1997 ident: WOS:000071491900011 article-title: A concise synthesis of arnottin I via internal biaryl coupling reaction using palladium reagent publication-title: HETEROCYCLES contributor: fullname: Harayama, T – volume: 38 start-page: 1229 year: 1999 ident: WOS:000080170100010 article-title: Total synthesis of pradimicinone, the common aglycon of the pradimicin-benanomicin antibiotics publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Kitamura, M – volume: 44 start-page: 8665 year: 2003 ident: WOS:000186474400007 article-title: Rhodium-HMPT-catalyzed direct ortho arylation of phenols with aryl bromides publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2003.09.151 contributor: fullname: Oi, S – volume: 125 start-page: 1698 year: 2003 ident: WOS:000181088000009 article-title: A ruthenium-catalyzed reaction of aromatic ketones with arylboronates: A new method for the arylation of aromatic compounds via C-H bond cleavage publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja029273f contributor: fullname: Kakiuchi, F – volume: 60 start-page: 8101 year: 1995 ident: WOS:A1995TH61000064 article-title: SOME OBSERVATIONS ON THE PALLADIUM-CATALYZED TRIFLATE-ARENE CYCLIZATION OF ELECTRON-RICH BIARYL SUBSTRATES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: RICE, JE – volume: 5 start-page: 301 year: 2003 ident: WOS:000180766400018 article-title: Regioselective palladium-catalyzed arylation of 3-carboalkoxy furan and thiophene publication-title: ORGANIC LETTERS doi: 10.1021/ol027266q contributor: fullname: Glover, B – volume: 125 start-page: 5274 year: 2003 ident: WOS:000182682700014 article-title: Selective C-arylation of free (NH)-heteroarenes via catalytic C-H bond functionalization (Retracted Article. See vol 128, pg 8364, 2006) publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja034848+ contributor: fullname: Sezen, B – volume: 7 start-page: 2341 year: 2001 ident: WOS:000169209900008 article-title: Intramolecular C-H activation by alkylpalladium(II) complexes: Insights into the mechanism of the palladium-catalyzed arylation reaction publication-title: CHEMISTRY-A EUROPEAN JOURNAL contributor: fullname: Martin-Matute, B – volume: 43 start-page: 2201 year: 2004 ident: WOS:000221040600004 article-title: Rational ligand design in constructing efficient catalyst systems for Suzuki-Miyaura coupling publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200301753 contributor: fullname: Miura, M – volume: 36 start-page: 1740 year: 1997 ident: WOS:A1997XX18100020 article-title: Palladium-catalyzed regioselective mono- and diarylation reactions of 2-phenylphenols and naphthols with aryl halides publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH contributor: fullname: Satoh, T – start-page: 2439 year: 1998 ident: WOS:000077083700009 article-title: Rhodium-catalysed direct ortho arylation of 2-arylpyridines with arylstannanes via C-H activation publication-title: CHEMICAL COMMUNICATIONS contributor: fullname: Oi, S – volume: 114 start-page: 3568 year: 1992 ident: WOS:A1992HQ81400069 article-title: TOTAL SYNTHESIS AND ABSOLUTE STEREOCHEMICAL ASSIGNMENT OF GILVOCARCIN-M publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: MATSUMOTO, T – volume: 44 start-page: 8149 year: 2003 ident: WOS:000185941000024 article-title: Intramolecular ortho-arylation of phenols utilized in the synthesis of the aporphine alkaloids (+/-)-lirinidine and (+/-)-nuciferine publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2003.09.026 contributor: fullname: Cuny, GD – volume: 42 start-page: 112 year: 2003 ident: WOS:000180458100024 article-title: The catalytic intermolecular orthoarylation of phenols publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Bedford, RB – volume: 65 start-page: 7187 year: 2000 ident: WOS:000165199000052 article-title: Annulation strategies for benzo[b]fluorene synthesis: Efficient routes to the kinafluorenone and WS-5995 antibiotics publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Qabaja, G – volume: 126 start-page: 7460 year: 2004 ident: ja049017yb00006/ja049017yb00006_1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja047980y contributor: fullname: After – volume: 64 start-page: 6019 year: 1999 ident: ja049017yb00010/ja049017yb00010_1 publication-title: J. Org. Chem. doi: 10.1021/jo990568u contributor: fullname: Harris M. C. – volume: 425 start-page: 151 year: 1992 ident: ja049017yb00015/ja049017yb00015_2 publication-title: J. Organomet. Chem. doi: 10.1016/0022-328X(92)80031-R contributor: fullname: Catellani M. – volume: 2 start-page: 200 year: 1964 ident: ja049017yb00017/ja049017yb00017_1 publication-title: Adv. Phys. Org. Chem. contributor: fullname: Zollinger H. – volume: 102 start-page: 1359 year: 2002 ident: ja049017yb00001/ja049017yb00001_1 publication-title: Chem. Rev. doi: 10.1021/cr000664r contributor: fullname: For – volume: 42 start-page: 112 year: 2003 ident: ja049017yb00003/ja049017yb00003_1 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200390037 contributor: fullname: Current – volume: 125 start-page: 12084 year: 2003 ident: ja049017yb00016/ja049017yb00016_1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja037546g contributor: fullname: For – volume: 125 start-page: 5274 year: 2003 ident: ja049017yb00002/ja049017yb00002_1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja034848+ contributor: fullname: For – volume: 38 start-page: 1229 year: 1999 ident: ja049017yb00004/ja049017yb00004_1 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/(SICI)1521-3773(19990503)38:9<1229::AID-ANIE1229>3.0.CO;2-B contributor: fullname: With – volume: 43 start-page: 2201 year: 2004 ident: ja049017yb00012/ja049017yb00012_1 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.200301753 contributor: fullname: For – volume: 40 start-page: 1919 year: 1984 ident: ja049017yb00008/ja049017yb00008_1 publication-title: Tetrahedron doi: 10.1016/S0040-4020(01)91149-4 contributor: fullname: Ames – volume: 62 start-page: 2 year: 1997 ident: ja049017yb00007/ja049017yb00007_1 publication-title: J. Org. Chem. doi: 10.1021/jo961876k contributor: fullname: Hennings D. D. – volume: 41 start-page: 1063 year: 2000 ident: ja049017yb00005/ja049017yb00005_1 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(99)02235-2 contributor: fullname: Futagami S. – volume: 7 start-page: 2341 year: 2001 ident: ja049017yb00015/ja049017yb00015_1 publication-title: Chem. Eur. J. doi: 10.1002/1521-3765(20010601)7:11<2341::AID-CHEM23410>3.0.CO;2-S contributor: fullname: Martin-Matute B. |
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Snippet | In this Communication, we describe direct arylation reactions with improved scope and catalyst activity for the intramolecular formation of biaryl compounds.... |
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SubjectTerms | Chemistry Chemistry, Multidisciplinary Exact sciences and technology Organic chemistry Physical Sciences Science & Technology |
Title | Biaryl Synthesis via Direct Arylation: Establishment of an Efficient Catalyst for Intramolecular Processes |
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