Synthesis and C2-functionalization of indoles with allylic acetates under rhodium catalysis

Abstract

Tandem rhodium-catalyzed oxidative allylation and annulation of acetanilides with allyl acetate to afford the corresponding indoles are described. In addition, the site-selective C2 allylation, crotylation and prenylation of indoles using allylic acetates under rhodium catalysis are reported.

Indole synthesis through transition metal-catalyzed C–H activation

“…Acetanilides reacted with allyl acetates to afford N-Ac indoles under Rh(III) catalysis. 53 Heterogenous ceria-supported ruthenium catalysts effected the synthesis of indole (> 99%) via dehydrogenative N-heterocyclization (Scheme 37). 54 …”

Regioselective N-allylation and N-cinnamylation of indoles using CuI-exchanged hierarchical nanoporous material

“…Regioselective C-2 allylation of indoles has also been achieved by the use of catalysts such as Potassium organotrifluoroborate salts [7], Pd [8] and Rh [9] catalysts. Similarly selective synthesis of C-3 allylated indoles includes the use of catalysts such as H 2 SO 4 [10], Ru [11], amberlyst-15 [12], Et 3 B [13], Pd [14][15].…”

Synthesis of substituted allyl acetates from heterocyclic dienes by Pd-promoted arylation-acetoxylation cascade

“…[2-(4-Methylbenzyl)- 1,4,6,7,12,12b-hexahydroindolo[2,3-a]quinolizin-3-yl]methyl acetate (9). Compound was synthesised from diene 8 and 4-iodotoluene following the general 1340 S I M I Ć et al…”

“…[1][2][3][4][5] Their reactions promoted by different transition metals are of particular interest. [6][7][8][9][10][11][12][13] Amongst them, Pd-catalysed processes stand as the most intensively studied methodologies frequently used in the synthesis of various organic molecules, including naturally occurring substances. [14][15][16][17][18][19][20][21][22] The most common way to access allylic acetates utilizes allyl alcohols as starting materials, which are widely accessible via addition of vinyl-nucleophiles on aldehydes or ketones or simple nucleophilic additions on α,β-unsaturated equivalents.…”