@article{f6f32fd51fcb42318e7f238321d3b710,
title = "Me2AlCl-mediated carboxylation, ethoxycarbonylation, and carbamoylation of indoles",
abstract = "Various 1-methyl-, 1-triisopropylsilyl-, and 1-benzylindoles are carboxylated under CO2 pressure (3.0 MPa) with the aid of 1.0 molar equiv of Me2AlCl to give 1-substituted indole-3-carboxylic acids in good to excellent yields. Mechanistic studies suggest that the intermediate, an indol-3-ylaluminum ate complex, was reversibly formed by electrophilic addition of Me2AlCl to the substrate followed by deprotonation of the resulting adduct. This method is successfully extended to alkoxycarbonylation with ethyl chloroformate and carbamoylation with naphthalen-1-yl isocyanate, which afford ethyl indole-3-carboxylates and N-naphthalen-1-ylindole-3-carboxamides, respectively.",
keywords = "Alkoxycarbonylation, Alumination, Carbamoylation, Carboxylation, Indole",
author = "Koji Nemoto and Shinya Tanaka and Megumi Konno and Satoru Onozawa and Masafumi Chiba and Yuuki Tanaka and Yosuke Sasaki and Ryo Okubo and Tetsutaro Hattori",
note = "Funding Information: This study was supported in part by a Grant-in-Aid for Scientific Research on a Priority Area {\textquoteleft}Advanced Molecular Transformations of Carbon Resources{\textquoteright} from the Ministry of Education, Culture, Sports, Science, and Technology , Japan. T.H. thanks Kazuo Tanaka, the Koheleth private foundation for financial support. Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd. All rights reserved.",
year = "2016",
month = feb,
day = "4",
doi = "10.1016/j.tet.2015.12.028",
language = "English",
volume = "72",
pages = "734--745",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "5",
}