Palladium‐Catalyzed Construction of Heteroatom‐Containing π‐Conjugated Systems by Intramolecular Oxidative CH/CH Coupling Reaction

Abstract

Synthesis of heteroatom-containing ladder-type π-conjugated molecules was successfully achieved via a palladium-catalyzed intramolecular oxidative C-H/C-H cross-coupling reaction. This reaction provides a variety of π-conjugated molecules bearing heteroatoms, such as nitrogen, oxygen, phosphorus, and sulfur atoms, and a carbonyl group. The π-conjugated molecules were synthesized efficiently, even in gram scale, and larger π-conjugated molecules were also obtained by a double C-H/C-H cross-coupling reaction and successive oxidative cycloaromatization.

Photoluminescent arginine‐functionalized polycitrate with enhanced cell activity and hemocompatibility for live cell bioimaging

“…In recent years, it was shown that some nonconjugated polymers containing amine group such as poly(amidoamine) showed excellent fluorescent emission . Further studies exhibited that the heteroatom‐containing double bonds in these nonconjugated polymers may contribute to their excellent photoluminescent performance . The detailed fluorescent mechanism of amine‐contained nonconjugated polymers is still under investigation.…”

A new route towards dithienoquinazoline and benzo[f]thieno[3,2-h]quinazoline systems using Pd-catalyzed intramolecular cyclization under microwave irradiation

“…Thus, incomplete conversion of the starting reagents 3 and 4 into target products 5 was observed even after long reaction times (up to 2 weeks). In all cases, the starting reagent 3a-g was partially recovered after the reaction was stopped (see Table 1, entries [8][9][10][11][12][13][14][15]. Mercury 25 representation of the X-ray crystal structure of 5a with thermal ellipsoids of 50% probability.…”

“…[6][7][8][9][10] Palladium-catalyzed C-H intermolecular and/or intramolecular arylation offers one of the most efficient and reliable methods for the construction of different polycyclic structures. [11][12][13][14][15] In this communication, we present a new and simple route to dithienoquinazoline and benzo [f]thieno [3,2-h]quinazoline systems I-III, based on Pd-catalyzed intramolecular cyclization, proceeding under microwave irradiation.…”

The Development of Novel C-H Bond Transformations and Their Application to the Synthesis of Organic Functional Molecules

“…Another strategy for the synthesis of heteroatom containing π conjugated molecules is C H/C H coupling reaction of heteroatom bridged biaryl compounds (Scheme 19). 31,32 This reaction provided a variety of π conjugated molecules bearing heteroatoms, such as nitrogen, oxygen, phosphorus, and sulfur atoms, and in some cases also a carbonyl group. The π conjugated molecules were synthesized ef ciently, even on a gram scale, and larger π conjugated mole cules could also be obtained by a double C H/C H cross coupling reaction and subsequent oxidative cycloaromatization (Scheme 19, bottom row).…”