The Copper-Catalyzed N-Arylation of Indoles

Abstract

A general method for the N-arylation of indoles using catalysts derived from CuI and trans-1,2-cyclohexanediamine (1a), trans-N,N'-dimethyl-1,2-cyclohexanediamine (2a), or N,N'-dimethyl-ethylenediamine (3) is reported. N-Arylindoles can be produced in high yield from the coupling of an aryl iodide or aryl bromide with a variety of indoles.

C-2/C-3 Annulation and C-2 Alkylation of Indoles with 2-Alkoxycyclopropanoate Esters

“…Recent examples of indole functionalization include asymmetric C-3 Friedel-Craft reactions, 1,2,3 allylations, 4,5 radical couplings, 6 arylations, 7,8,9 Michael-additions, 10 C-H activation, 11 and N-arylations. 12 Indoles containing a fused 5-membered ring at the C-2 and C-3 positions are well represented in nature, and include the penitrems 13 and kopsane 14 alkaloids. 15 In this regard, it has been reported by Kerr and co-workers that the annulation of indoles with 1,3-dipoles is a successful strategy for rapidly increasing the molecular complexity by simultaneous functionalization of C-2 and C-3, although yields for the annulation products are generally modest.…”

Highly efficient copper-catalyzed N-arylation of alkylamines with aryl iodides using phosphoramidite as ligand

“…However, the copper-mediated reaction in mild conditions has become a focus of research for large and industrial-scale production from an economic point of view [8][9][10][11]. Recently, many ligands, such as 1,10-phenanthroline [12][13][14][15][16], trans-1,2-cyclohexadiamine [17][18][19][20][21], ethylene glycol [22,23], amino acid [24,25], and other nitrogen, oxygencontaining ligands [26][27][28][29] have been developed under mild condition in copper-catalyzed aminations. However, only several papers have contributed to N-arylation of alkylamines and just a few ligands were found to be effective in these transformation [30][31][32][33].…”

Copper‐Catalyzed Stereoselective Hydroarylation of 3‐Aryl‐2‐ propynenitriles with Arylboronic Acids

“…The isolated 4ag was subjected to Ullmann coupling with slightly excess amounts of indole according to the procedures reported by Buchwald and co-workers. [12] In the presence of 5 mol% CuI, 20 mol% N,N'-dimethylethylenediamine (DMEDA), and K 3 PO 4 , 4ag and indole were refluxed in toluene for 24 h to obtain 6 in 86% yield. No erosion of olefin stereochemistry was observed for the isolated 6.…”