Chemo- and regio-selective amidation of indoles with isocyanates using borane Lewis acids

Ayan Dasgupta, Michael G. Guerzoni, Nusaybah Alotaibi, Yara van Ingen, Kaveh Farshadfar, Emma Richards*, Alireza Ariafard, Rebecca L. Melen

*Tämän työn vastaava kirjoittaja

Tutkimustuotos: LehtiartikkeliArticleScientificvertaisarvioitu

2 Sitaatiot (Scopus)
32 Lataukset (Pure)

Abstrakti

The efficacy of boron-based catalysts has drawn considerable attention from the scientific community due to their relatively low toxicities and high selectivities. Formation of a new carbon-carbon or carbon-nitrogen bond to generate an amide/urea functionality using mild, catalytic reaction protocols has always been an important challenge, as functionalised amides and urea derivatives are important scaffolds in medicinal chemistry. Herein we report a facile and mild catalytic reaction protocol towards the amidation of N-methyl indoles/pyrroles (17 examples, yields up to 58%) using B(C6F5)3 (30 mol%). Moreover, our investigation revealed that although catalytic amounts of B(C6F5)3 (10 mol%) are efficient towards the N-carboxamidation of unprotected indoles, catalytic BCl3 (5 mol%) is capable of producing near quantitative yields of the N-carboxamidation products (21 examples, yields up to 95%). In contrast with previous literature reports, the reaction between 2-(alkynyl)anilines and aryl isocyanates using catalytic BCl3 (5 mol%) afforded N-H inserted products (9 examples, yields up to 71%) chemo-selectively as opposed to the intramolecular hydroamination product. Comprehensive DFT studies have been undertaken to understand the mechanistic details of the N-H functionalisation of indoles.

AlkuperäiskieliEnglanti
Sivut5982-5990
JulkaisuCatalysis Science and Technology
Vuosikerta12
Numero19
Varhainen verkossa julkaisun päivämäärä25 elok. 2022
DOI - pysyväislinkit
TilaJulkaistu - 7 lokak. 2022
OKM-julkaisutyyppiA1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä

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