The Double N‐Arylation of Primary Amines: Toward Multisubstituted Carbazoles with Unique Optical Properties

Abstract

A powerful method: A variety of sterically crowded, substituted carbazoles have been prepared from anilines and biphenyl compounds (see scheme). The method enabled the preparation of 2,2′‐dicarbazolyl‐1,1′‐biaryl compounds, which show excimer (or exciplex) emissions with significant solvent dependency.

Highly Efficient and Stable Red Phosphorescent Organic Light‐Emitting Diodes Using Platinum Complexes

“…TLEC‐025 and TLEC‐027 (supplied by Takasago International Corporation) were synthesized by previously reported methods15, 16 (see Supporting Information). Recently, an efficient method of synthesizing a similar platinum complex was proposed by Suzuki et al17 TLEC‐025 and TLEC‐027 (shown in Figure ) were designed to have a more rigid structure than previously reported platinum complexes, such as [[2,2′‐[1,2‐phenylenebis(nitrilomethylidyne)]bis[4,6‐di‐ tert ‐butylphenolate]]‐ N , N ′, O , O ′] platinum (II) (Pt‐SA‐1) 14.…”

Synthesis of N‐Arylcarbazoles by Palladium‐Catalyzed Direct C–H Arylation of 2‐(Diarylamino)phenyl Triflates

“…One of these alternatives is the intermolecular Buchwald–Hartwig aryl amination . Nozaki reported an interesting extension involving the twofold Buchwald–Hartwig aryl amination of anilines and 2,2′‐halobiphenyl . Even though more focus has recently been placed on the investigation of transition‐metal‐free routes to N ‐arylcarbazoles, transition‐metal‐promoted protocols still play an important role.…”

Convenient Synthesis of 11‐Substituted 11H‐Indolo[3,2‐c]quinolines by Sequential Chemoselective Suzuki Reaction/Double C–N Coupling

“…In our approach, the substituents located at the 11‐position are installed directly, thereby avoiding the problem of selectivity in the alkylation of the 11‐unsubstituted heterocycle. Our methodology is based on chemoselective Suzuki reactions of 3,4‐dihalo‐2‐methylquinolines with o ‐bromophenylboronic acid …”