Copper/β-diketone-catalysed N-arylation of carbazoles

Abstract

A copper/β-diketone-catalysedN-arylation of carbazoles with aryl iodides is developed with broad substrate applicability and moderate to good yields.

High‐Efficiency Sky Blue to Ultradeep Blue Thermally Activated Delayed Fluorescent Diodes Based on Ortho‐Carbazole‐Appended Triarylboron Emitters: Above 32% External Quantum Efficiency in Blue Devices

“…Commercial reagents and spectrophotometric‐grade toluene were used as received. 3,6‐Di‐ tert ‐butyl‐9‐(2‐bromophenyl)‐9 H ‐carbazole and 9‐(2‐(dimesitylboryl)phenyl)‐9 H ‐carbazole (Cz o B, 3 ) were prepared based on the reported procedures. Deuterated solvents from Cambridge Isotope Laboratories were used.…”

Base-Promoted SNAr Reactions of Fluoro- and Chloroarenes as a Route to N-Aryl Indoles and Carbazoles

“…N-Phenylcarbazole ( 5a ) [37]: White solid (from 2j , 121.6 mg, 70%); 1 H-NMR (400 MHz, CDCl 3 ) δ 8.15 (d, J = 7.7 Hz, 2H), 7.65–7.54 (m, 4H), 7.47 (t, J = 7.1 Hz, 1H), 7.41 (d, J = 4.0 Hz, 4H), 7.33–7.27 (m, 2H); 13 C-NMR (100 MHz, CDCl 3 ) δ 141.0, 137.8, 129.9, 127.5, 127.2, 126.0, 123.4, 120.4, 120.0, 109.8; GC-MS m / z : 243 (M + ).…”

“…N-(3-Fluorophenyl)carbazole ( 5e ) [37]: White solid (177.6 mg, 68%); 1 H-NMR (400 MHz, CDCl 3 ) δ 8.11 (d, J = 7.7 Hz, 2H), 7.57–7.47 (m, 1H), 7.46–7.24 (m, 8H), 7.21–7.08 (m, 1H); 13 C-NMR (100 MHz, CDCl 3 ) δ 163.5 (d, J C-F = 246.0 Hz), 140.6, 139.4 (d, J C-F = 10.0 Hz), 131.2 (d, J C-F = 9.0 Hz), 126.2, 123.6, 122.4 (d, J C-F = 6.0 Hz), 120.5, 120.4, 114.6 (d, J C-F = 7.0 Hz), 114.4 (d, J C-F = 9.0 Hz), 109.8; GC-MS m / z : 261 (M + ).…”

“…N-(2-Fluorophenyl)carbazole ( 5f ) [37]: White waxy oil (148.9 mg, 57%); 1 H-NMR (400 MHz, CDCl 3 ) δ 8.25 (d, J = 8.2 Hz, 2H), 7.72 (t, J = 7.8 Hz, 1H), 7.68–7.57 (m, 2H), 7.50 (t, J = 7.4 Hz, 1H), 7.43 (t, J = 7.7 Hz, 2H), 7.30 (t, J = 7.4 Hz, 2H), 7.19 (d, J = 8.2 Hz, 2H); 13 C-NMR (100 MHz, CDCl 3 ) δ 157.6 (d, J C-F = 248.0 Hz), 140.2, 130.5 (d, J C-F = 7.0 Hz), 129.9, 126.4, 125.9 (d, J C-F = 3.0 Hz), 124.0 (d, J C-F = 13.0 Hz), 122.8, 120.5, 120.3, 117.4 (d, J C-F = 19.0 Hz), 109.6; HRMS (ESI): m / z Calcd. For: C 18 H 12 FN [M + H] + : 262.1027; found 262.1025.…”

“…In continuation of our interest in the development of highly atom-economic reactions through C-Cl bond activation in aryl chlorides and their transformation [27,28,29,30,31,32], we have investigated the N -arylation of indoles and carbazole by the nucleophilic aromatic substitution ( S N Ar ) protocol from chloroarenes and fluoroarenes in the presence of KOH in DMSO. The N -arylation of indoles and carbazoles through transition- metal-catalyzed catalysis have been well studied [33,34,35,36,37,38], and a microwave-assisted N -arylation of indoles via S N Ar in the presence of K 2 CO 3 or Cs 2 CO 3 under microwave irradiation in DMSO [39], KO t Bu-promoted N -arylations of carbazoles using diaryliodonium salts [40] have also been reported.…”