{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,14]],"date-time":"2026-10-14T22:03:56Z","timestamp":1792015436860,"version":"4.4.0"},"reference-count":55,"publisher":"American Chemical Society (ACS)","issue":"24","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Org. Chem."],"published-print":{"date-parts":[[2006,11,1]]},"DOI":"10.1021\/jo0614339","type":"journal-article","created":{"date-parts":[[2006,11,3]],"date-time":"2006-11-03T06:02:14Z","timestamp":1162533734000},"page":"9088-9095","source":"Crossref","is-referenced-by-count":324,"title":["Nucleophilic Reactivities of Indoles"],"prefix":"10.1021","volume":"71","author":[{"given":"Sami","family":"Lakhdar","sequence":"first","affiliation":[{"name":"Laboratoire SIRCOB, UMR 8180, Institut Lavoisier, Universit\u00e9 de Versailles, 45, Avenue des Etats-Unis, 78035 Versailles Cedex, France, Unit\u00e9 de Recherche, Chimie Th\u00e9orique et R\u00e9activit\u00e9, Universit\u00e9 de Monastir, Facult\u00e9 des Sciences de Monastir, Boulevard de l'environnement, 5019 Monastir, Tunisia, and Department Chemie und Biochemie, Ludwig-Maximilians-Universit\u00e4t M\u00fcnchen, Butenandtstrasse 5-13 (Haus F), 81377 M\u00fcnchen, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Martin","family":"Westermaier","sequence":"additional","affiliation":[{"name":"Laboratoire SIRCOB, UMR 8180, Institut Lavoisier, Universit\u00e9 de Versailles, 45, Avenue des Etats-Unis, 78035 Versailles Cedex, France, Unit\u00e9 de Recherche, Chimie Th\u00e9orique et R\u00e9activit\u00e9, Universit\u00e9 de Monastir, Facult\u00e9 des Sciences de Monastir, Boulevard de l'environnement, 5019 Monastir, Tunisia, and Department Chemie und Biochemie, Ludwig-Maximilians-Universit\u00e4t M\u00fcnchen, Butenandtstrasse 5-13 (Haus F), 81377 M\u00fcnchen, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fran\u00e7ois","family":"Terrier","sequence":"additional","affiliation":[{"name":"Laboratoire SIRCOB, UMR 8180, Institut Lavoisier, Universit\u00e9 de Versailles, 45, Avenue des Etats-Unis, 78035 Versailles Cedex, France, Unit\u00e9 de Recherche, Chimie Th\u00e9orique et R\u00e9activit\u00e9, Universit\u00e9 de Monastir, Facult\u00e9 des Sciences de Monastir, Boulevard de l'environnement, 5019 Monastir, Tunisia, and Department Chemie und Biochemie, Ludwig-Maximilians-Universit\u00e4t M\u00fcnchen, Butenandtstrasse 5-13 (Haus F), 81377 M\u00fcnchen, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"R\u00e9gis","family":"Goumont","sequence":"additional","affiliation":[{"name":"Laboratoire SIRCOB, UMR 8180, Institut Lavoisier, Universit\u00e9 de Versailles, 45, Avenue des Etats-Unis, 78035 Versailles Cedex, France, Unit\u00e9 de Recherche, Chimie Th\u00e9orique et R\u00e9activit\u00e9, Universit\u00e9 de Monastir, Facult\u00e9 des Sciences de Monastir, Boulevard de l'environnement, 5019 Monastir, Tunisia, and Department Chemie und Biochemie, Ludwig-Maximilians-Universit\u00e4t M\u00fcnchen, Butenandtstrasse 5-13 (Haus F), 81377 M\u00fcnchen, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Taoufik","family":"Boubaker","sequence":"additional","affiliation":[{"name":"Laboratoire SIRCOB, UMR 8180, Institut Lavoisier, Universit\u00e9 de Versailles, 45, Avenue des Etats-Unis, 78035 Versailles Cedex, France, Unit\u00e9 de Recherche, Chimie Th\u00e9orique et R\u00e9activit\u00e9, Universit\u00e9 de Monastir, Facult\u00e9 des Sciences de Monastir, Boulevard de l'environnement, 5019 Monastir, Tunisia, and Department Chemie und Biochemie, Ludwig-Maximilians-Universit\u00e4t M\u00fcnchen, Butenandtstrasse 5-13 (Haus F), 81377 M\u00fcnchen, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Armin R.","family":"Ofial","sequence":"additional","affiliation":[{"name":"Laboratoire SIRCOB, UMR 8180, Institut Lavoisier, Universit\u00e9 de Versailles, 45, Avenue des Etats-Unis, 78035 Versailles Cedex, France, Unit\u00e9 de Recherche, Chimie Th\u00e9orique et R\u00e9activit\u00e9, Universit\u00e9 de Monastir, Facult\u00e9 des Sciences de Monastir, Boulevard de l'environnement, 5019 Monastir, Tunisia, and Department Chemie und Biochemie, Ludwig-Maximilians-Universit\u00e4t M\u00fcnchen, Butenandtstrasse 5-13 (Haus F), 81377 M\u00fcnchen, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Herbert","family":"Mayr","sequence":"additional","affiliation":[{"name":"Laboratoire SIRCOB, UMR 8180, Institut Lavoisier, Universit\u00e9 de Versailles, 45, Avenue des Etats-Unis, 78035 Versailles Cedex, France, Unit\u00e9 de Recherche, Chimie Th\u00e9orique et R\u00e9activit\u00e9, Universit\u00e9 de Monastir, Facult\u00e9 des Sciences de Monastir, Boulevard de l'environnement, 5019 Monastir, Tunisia, and Department Chemie und Biochemie, Ludwig-Maximilians-Universit\u00e4t M\u00fcnchen, Butenandtstrasse 5-13 (Haus F), 81377 M\u00fcnchen, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2006,11,3]]},"reference":[{"key":"jo0614339b00001\/jo0614339b00001_1","unstructured":"(a) Sundberg, R. J.\n                      Indoles\n                      ; Academic Press:\u2009 San Diego, 1996; p 190."},{"key":"jo0614339b00001\/jo0614339b00001_2","unstructured":"(b) Sundberg, R. J.\n                      The Chemistry of Indoles\n                      ; Academic Press:\u2009 New York, 1970; p 489."},{"key":"jo0614339b00001\/jo0614339b00001_3","first-page":"376","volume-title":"Comprehensive Heterocyclic Chemistry","volume":"4","author":"Sundberg R.","year":"1984"},{"key":"jo0614339b00001\/jo0614339b00001_4","volume-title":"The Chemistry of Heterocyclic Compounds","author":"Remers W.","year":"1972"},{"key":"jo0614339b00001\/jo0614339b00001_5","doi-asserted-by":"crossref","first-page":"590","DOI":"10.1039\/np9971400559","volume":"14","author":"Saxton J. E","year":"1997","journal-title":"Nat. Prod. Rep"},{"key":"jo0614339b00001\/jo0614339b00001_6","doi-asserted-by":"crossref","first-page":"340","DOI":"10.1039\/a815327y","volume":"15","author":"Toyota M.","year":"1998","journal-title":"Nat. Prod. Rep"},{"key":"jo0614339b00002\/jo0614339b00002_1","doi-asserted-by":"crossref","first-page":"2666","DOI":"10.1021\/cr020086+","volume":"104","author":"Makosza M.","year":"2004","journal-title":"Chem. Rev"},{"key":"jo0614339b00002\/jo0614339b00002_2","doi-asserted-by":"crossref","unstructured":"(b) Makosza, M.; Wojciechowski, K.\n                      Heterocycles\n                      2001\n                      ,\n                      54\n                      , 445\u2212474.","DOI":"10.3987\/REV-00-SR(I)2"},{"key":"jo0614339b00002\/jo0614339b00002_3","unstructured":"(c) Makosza, M.; Wojciechowski, K. In\n                      The Chemistry of Synthetic Indole Systems\n                      ; Kartsev, V. G., Ed.; Interbioscreen Monograph Series; IBS Press:\u2009 Moscow, 2004; Vol. 3, pp 103\u2212143."},{"key":"jo0614339b00003\/jo0614339b00003_1","first-page":"1672","volume":"2","author":"Terrier F.","year":"1993","journal-title":"J. Chem. Soc., Perkin Trans."},{"key":"jo0614339b00004\/jo0614339b00004_1","unstructured":"General reviews:\u2009 (a) Mayr, H.; Kempf, B.; Ofial, A. R.\n                      Acc. Chem.\n                      Res.\n                      2003\n                      ,\n                      36\n                      , 66\u221277. (b) Mayr, H.; Patz, M.\n                      Angew. Chem.\n                      1994\n                      ,\n                      106\n                      , 990\u22121010;\n                      Angew. Chem., Int. Ed. Engl.\n                      1994\n                      ,\n                      33\n                      , 938\u2212957. (c) Mayr, H.; Patz, M.; Gotta, M. F.; Ofial, A. R.\n                      Pure Appl. Chem.\n                      1998\n                      ,\n                      70\n                      , 1993\u22122000. (d) Mayr, H.; Ofial, A. R. In\n                      Carbocation Chemistry\n                      ; Olah, G. A., Prakash, G. K. S., Eds.; Wiley:\u2009 Hoboken, 2004; Chapter 13, pp 331\u2212358. (e) Mayr, H.; Ofial, A. R.\n                      Pure Appl. Chem.\n                      2005\n                      ,\n                      77\n                      , 1807\u22121821. (f) Lucius, R.; Loos, R.; Mayr, H.\n                      Angew. Chem.\n                      2002\n                      ,\n                      114\n                      , 97\u2212102;\n                      Angew. Chem., Int. Ed.\n                      2002\n                      ,\n                      41\n                      , 91\u221295."},{"key":"jo0614339b00005\/jo0614339b00005_1","volume-title":"Engl","author":"Nucleophilicities","year":"1992"},{"key":"jo0614339b00006\/jo0614339b00006_1","first-page":"801","volume":"799","author":"Li D. P.","year":"2006","journal-title":"Chem. Commun"},{"key":"jo0614339b00006\/jo0614339b00006_2","doi-asserted-by":"crossref","first-page":"3089","DOI":"10.1002\/anie.200462877","volume":"44","author":"T\u00f6r\u00f6k B.","year":"2005","journal-title":"Angew. Chem., Int. Ed"},{"key":"jo0614339b00006\/jo0614339b00006_3","first-page":"8157","volume":"128","author":"Wang Y. Q.","year":"2006","journal-title":"J. Am. Chem. Soc"},{"key":"jo0614339b00006\/jo0614339b00006_4","first-page":"2118","volume":"8","author":"Lu S. F.","year":"2006","journal-title":"Org. Lett"},{"key":"jo0614339b00007\/jo0614339b00007_1","doi-asserted-by":"crossref","first-page":"9512","DOI":"10.1021\/ja010890y","volume":"123","author":"Mayr H.","year":"2001","journal-title":"J. Am. Chem. Soc"},{"key":"jo0614339b00007\/jo0614339b00007_2","doi-asserted-by":"crossref","first-page":"3959","DOI":"10.1002\/ange.200600008","volume":"118","author":"Phan T. B.","year":"2006","journal-title":"Angew. Chem"},{"key":"jo0614339b00008\/jo0614339b00008_1","first-page":"2218","volume":"9","author":"Kempf B.","year":"2003","journal-title":"Chem. Eur. J"},{"key":"jo0614339b00010\/jo0614339b00010_1","doi-asserted-by":"crossref","first-page":"707","DOI":"10.1002\/(SICI)1099-1395(1998100)11:10<707::AID-POC37>3.0.CO;2-V","volume":"11","author":"Terrier F.","year":"1998","journal-title":"J. Phys. Org. Chem"},{"key":"jo0614339b00010\/jo0614339b00010_2","doi-asserted-by":"crossref","first-page":"5537","DOI":"10.1021\/jo060437a","volume":"71","author":"Forlani L.","year":"2006","journal-title":"J. Org. Chem"},{"key":"jo0614339b00011\/jo0614339b00011_1","volume-title":"Electrophilic Aromatic Substitutions","author":"Taylor R.","year":"1980"},{"key":"jo0614339b00011\/jo0614339b00011_2","first-page":"1488","volume":"2","author":"Jackson A. H.","year":"1987","journal-title":"J. Chem. Soc., Perkin Trans."},{"key":"jo0614339b00012\/jo0614339b00012_1","first-page":"1217","volume":"2","author":"Challis B. C.","year":"1975","journal-title":"J. Chem. Soc., Perkin Trans."},{"key":"jo0614339b00012\/jo0614339b00012_2","first-page":"1457","volume":"2","author":"Butler A. R.","year":"1977","journal-title":"J. Chem. Soc., Perkin Trans."},{"key":"jo0614339b00013\/jo0614339b00013_1","doi-asserted-by":"crossref","first-page":"1116","DOI":"10.1039\/p29720001116","volume":"2","author":"Challis B. C.","year":"1972","journal-title":"J. Chem. Soc., Perkin Trans."},{"key":"jo0614339b00013\/jo0614339b00013_2","first-page":"1119","volume":"2","author":"Challis B. C.","year":"1972","journal-title":"J. Chem. Soc., Perkin Trans."},{"key":"jo0614339b00013\/jo0614339b00013_3","first-page":"1624","volume":"2","author":"Challis B. C.","year":"1972","journal-title":"J. Chem. Soc., Perkin Trans."},{"key":"jo0614339b00013\/jo0614339b00013_4","doi-asserted-by":"crossref","first-page":"3806","DOI":"10.1021\/ja01072a040","volume":"86","author":"Hinman R. L.","year":"1964","journal-title":"J. Am. Chem. Soc"},{"key":"jo0614339b00014\/jo0614339b00014_1","doi-asserted-by":"crossref","first-page":"3200","DOI":"10.1021\/jo0015927","volume":"66","author":"Dilman A. D.","year":"2001","journal-title":"J. Org. Chem"},{"key":"jo0614339b00015\/jo0614339b00015_1","doi-asserted-by":"crossref","first-page":"4454","DOI":"10.1021\/ja00167a050","volume":"112","author":"Mayr H.","year":"1990","journal-title":"J. Am. Chem. Soc"},{"key":"jo0614339b00016\/jo0614339b00016_1","first-page":"6253","volume":"70","author":"The","year":"2005","journal-title":"J. Org. Chem"},{"key":"jo0614339b00017\/jo0614339b00017_1","doi-asserted-by":"crossref","first-page":"1742","DOI":"10.1021\/ja00031a031","volume":"114","author":"Terrier F.","year":"1992","journal-title":"J. Am. Chem. Soc"},{"key":"jo0614339b00018\/jo0614339b00018_1","doi-asserted-by":"crossref","first-page":"8670","DOI":"10.1021\/j100175a046","volume":"95","author":"Negrerie M.","year":"1991","journal-title":"J. Phys. Chem"},{"key":"jo0614339b00019\/jo0614339b00019_1","first-page":"770","volume":"766","author":"Salekh M. A.","year":"1988","journal-title":"Khim. Geterosikl. Soedin"},{"key":"jo0614339b00020\/jo0614339b00020_1","doi-asserted-by":"crossref","first-page":"495","DOI":"10.1021\/jo00380a003","volume":"52","author":"Buncel E.","year":"1987","journal-title":"J. Org. Chem"},{"key":"jo0614339b00020\/jo0614339b00020_2","doi-asserted-by":"crossref","first-page":"646","DOI":"10.1139\/v99-033","volume":"77","author":"Crampton M. R.","year":"1999","journal-title":"Can. J. Chem"},{"key":"jo0614339b00021\/jo0614339b00021_1","doi-asserted-by":"crossref","first-page":"4702","DOI":"10.1021\/jo00069a037","volume":"58","author":"Terrier F.","year":"1993","journal-title":"J. Org. Chem"},{"key":"jo0614339b00021\/jo0614339b00021_2","doi-asserted-by":"crossref","first-page":"309","DOI":"10.1071\/CH9830297","volume":"36","author":"Norris W. P.","year":"1983","journal-title":"Aust. J. Chem"},{"key":"jo0614339b00022\/jo0614339b00022_1","doi-asserted-by":"crossref","first-page":"3797","DOI":"10.1039\/a703128i","volume":"93","author":"Jennings P.","year":"1997","journal-title":"J. Chem. Soc., Faraday Trans"},{"key":"jo0614339b00023\/jo0614339b00023_1","doi-asserted-by":"crossref","first-page":"10912","DOI":"10.1021\/ja035191v","volume":"125","author":"Ofial A. R.","year":"2003","journal-title":"J. Am. Chem. Soc"},{"key":"jo0614339b00024\/jo0614339b00024_1","doi-asserted-by":"crossref","DOI":"10.1139\/v93-266","volume":"71","author":"Albar H. A.","year":"1993","journal-title":"Can. J. Chem"},{"key":"jo0614339b00025\/jo0614339b00025_1","first-page":"69","volume":"55","author":"Mayr H.","year":"1997","journal-title":"Liebigs Ann"},{"key":"jo0614339b00027\/jo0614339b00027_1","first-page":"543","volume":"84","author":"Kane-Maguire L. A. P.","year":"1984","journal-title":"Chem. Rev"},{"key":"jo0614339b00027\/jo0614339b00027_2","first-page":"2196","volume":"2192","author":"Kane-Maguire L. A. P.","year":"1976","journal-title":"J. Chem. Soc., Dalton Trans"},{"key":"jo0614339b00028\/jo0614339b00028_1","doi-asserted-by":"crossref","first-page":"312","DOI":"10.1021\/ja00288a004","volume":"107","author":"Terrier F.","year":"1985","journal-title":"J. Am. Chem. Soc"},{"key":"jo0614339b00029\/jo0614339b00029_1","first-page":"2402","volume":"2398","author":"Binks J. H.","year":"1957","journal-title":"J. Chem. Soc"},{"key":"jo0614339b00030\/jo0614339b00030_1","doi-asserted-by":"crossref","first-page":"69","DOI":"10.1002\/jlac.18993070104","volume":"307","author":"Drost P","year":"1899","journal-title":"Liebigs Ann. Chem"},{"key":"jo0614339b00031\/jo0614339b00031_1","first-page":"1674","volume":"2","author":"Crampton M. R.","year":"1999","journal-title":"J. Chem. Soc., Perkin Trans."},{"key":"jo0614339b00032\/jo0614339b00032_1","doi-asserted-by":"crossref","first-page":"3541","DOI":"10.1021\/jo00330a033","volume":"46","author":"Terrier F.","year":"1981","journal-title":"J. Org. Chem"},{"key":"jo0614339b00033\/jo0614339b00033_1","first-page":"1413","volume":"2","author":"Boga C.","year":"2001","journal-title":"J. Chem. Soc., Perkin Trans."},{"key":"jo0614339b00034\/jo0614339b00034_1","volume-title":"Nucleophilic Aromatic Displacement","author":"Terrier","year":"1991"},{"key":"jo0614339b00034\/jo0614339b00034_2","doi-asserted-by":"crossref","first-page":"5890","DOI":"10.1021\/ja00435a022","volume":"98","author":"Terrier F.","year":"1976","journal-title":"J. Am. Chem. Soc"},{"key":"jo0614339b00034\/jo0614339b00034_3","doi-asserted-by":"crossref","first-page":"152","DOI":"10.1021\/cr00048a001","volume":"82","author":"Terrier F","year":"1982","journal-title":"Chem. Rev"},{"key":"jo0614339b00035\/jo0614339b00035_1","doi-asserted-by":"crossref","first-page":"4181","DOI":"10.1021\/jo00196a016","volume":"49","author":"Terrier F.","year":"1984","journal-title":"J. Org. Chem"}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jo0614339","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,3,14]],"date-time":"2023-03-14T15:53:15Z","timestamp":1678809195000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/jo0614339"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2006,11,1]]},"references-count":55,"journal-issue":{"issue":"24","published-print":{"date-parts":[[2006,11,1]]}},"alternative-id":["10.1021\/jo0614339"],"URL":"https:\/\/doi.org\/10.1021\/jo0614339","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2006,11,1]]}}}