Palladium catalyzed dual C–H functionalization of indoles with cyclic diaryliodoniums, an approach to ring fused carbazole derivatives

Abstract

Palladium(II)-catalyzed dual C-H functionalization of indoles with cyclic diaryliodoniums was successfully achieved, providing a concise method to synthesize dibenzocarbazoles. In a single operation, two C-C bonds and one ring were formed. The reaction was ligand free and tolerated air and moisture conditions.

Copper‐Catalyzed Diphenylation of P(O)‐OH Bonds with Cyclic Diaryliodonium Salts

“…The collected solid was washed with Et 2 O three times, dried in vacuo to afford 1 a (1.68 g, 98 % yield) as a white powder. Compounds of 1 b – m were synthesized by the general procedure A , B , C. 1 a (yield: 81 %), 1 b (yield: 75 %), 1 c (yield: 69 %), 1 d (yield: 43 %), 1 e (yield: 65 %), 1 f (yield: 46 %), 1 g ((yield: 60 %), 1 i ((yield: 71 %), 1 j ((yield: 68 %), 1 l ((yield: 36 %), 1 m ((yield: 77 %), 1 h (yield: 29 %) and 1 k (yield: 55 %) are new compounds.…”

Atom Efficient Magnesiation of N‐Substituted Alkyl Indoles with a Mixed Sodium‐Magnesium Base

“…N ‐methylindole was purchased from Aldrich and stored over 4 Å molecular sieves. N ‐ethylindole, N ‐isopropylindole, n BuNa, and Mg(CH 2 SiMe 3 ) 2 were prepared according to literature procedures.…”

Atom‐Economical Applications of Diaryliodonium Salts

“…In 2014, Wen and co‐workers explored a Pd II ‐catalyzed dual C−H functionalization of indoles with cyclic diaryliodonium salts, providing an efficient method for the synthesis of dibenzocarbazoles (Scheme ) . Various N‐substituted functional groups on indoles, including a free indole without N‐position protection, were all tolerated.…”