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Using catalytic TsOH\u00b7H2O under mild conditions, the aza-FC reaction provides direct access to biologically relevant 3-(3,3-dialkylindolin-2-yl)indoles bearing an all-carbon quaternary center at the C3 position of the indoline ring. Despite the propensity of 3,3-disubstituted indolenines to undergo the competing Plancher rearrangement leading to the formation of the corresponding 2,3-disubstituted indoles, the desired aza-FC products were obtained with excellent chemoselectivity in most cases. The protocol accommodates a broad range of C3-unsubstituted indoles and both 3,3-diallyl- and 3,3-dibenzyl-substituted indolenines, affording the products in good to excellent yields (up to 85% over two steps) with good functional-group tolerance.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01739","type":"journal-article","created":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T11:01:55Z","timestamp":1790247715000},"page":"13482-13499","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis of 3-(2-Indolinyl)indoles\nvia Intermolecular\nAza-Friedel\u2013Crafts Reaction between 3,3-Disubstituted Indolenines\nand Indoles"],"prefix":"10.1021","volume":"91","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0070-713X","authenticated-orcid":true,"given":"Abhijit","family":"Gogoi","sequence":"first","affiliation":[{"name":"Tezpur University , , Napaam , Sonitpur, ,","place":["Tezpur, Assam, India, 784028"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jahnabi","family":"Das","sequence":"additional","affiliation":[{"name":"Tezpur University , , Napaam , Sonitpur, ,","place":["Tezpur, Assam, India, 784028"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1196-5863","authenticated-orcid":true,"given":"Sajal Kumar","family":"Das","sequence":"additional","affiliation":[{"name":"Tezpur University , , Napaam , Sonitpur, ,","place":["Tezpur, Assam, India, 784028"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,24]]},"reference":[{"key":"2026100909093495300_cit1a","doi-asserted-by":"publisher","DOI":"10.1002\/open.202200235","article-title":"Development\nand Application\nof Indolines in Pharmaceuticals","volume":"12","author":"Wei","year":"2023","journal-title":"ChemistryOpen"},{"key":"2026100909093495300_cit1b","doi-asserted-by":"publisher","first-page":"1721","DOI":"10.1039\/D2NP00030J","article-title":"Biosynthesis of pyrroloindoline-containing\nnatural products","volume":"39","author":"Sun","year":"2022","journal-title":"Nat. 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