Rh-catalysed divergent synthesis of polysubstituted pyrroles from α,β-unsaturated ketones via selective single or double insertion of isocyanides DOI
Takuya Shimbayashi,

Taiyou Ishige,

Ken‐ichi Fujita

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(22), P. 5559 - 5567

Published: Jan. 1, 2023

A novel divergent synthetic method for polysubstituted pyrroles from isocyanides and α,β-unsaturated ketones in the presence of a rhodium catalyst bis(pinacolato)diboron (B 2 pin ) is described here.

Language: Английский

Palladium-Catalyzed Imidoylation-Triggered [2 + 2 + 1] Cyclization of Internal Alkyne with Isocyanides DOI
Keke Huang, Jin‐Biao Liu, Zhifeng Chen

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(15), P. 5931 - 5935

Published: July 14, 2020

In this work, a palladium-catalyzed [2 + 2 1] cyclization of internal alkynes with double isocyanides is described. This facile procedure efficient for synthesizing various pyrrolo[3,2-c]quinolin-2-amines. The reaction worked well broad scope. the process, it believed that sequential isocyanide insertion, 6-exo-dig alkyne, and addition an imino group are involved.

Language: Английский

Citations

20
Palladium-Catalyzed Cycloaddition of Alkynylimines, Double Isocyanides, and H2O/KOAc DOI
Dianpeng Chen, Min Yang, Jianming Li

et al.

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(10), P. 6441 - 6449

Published: April 23, 2020

In this work, a palladium-catalyzed cyclization of alkynylimines and double isocyanides is described. This facile procedure efficient for synthesizing various 4-amidyl-2-aminopyrroles. Mechanism investigation indicates that four-membered ring-fused pyrrole species key intermediate the reaction involves [4 + 1] cycloaddition, protonation, nucleophilic addition, 1,4-addition isocyanide, rearomatization. Interestingly, linear dipyrrole derivative found to be an appropriate fluoride ion probe with remarkable emission change, which could serve as potential candidate optoelectronic conjugated materials.

Language: Английский

Citations

19
Copper-Catalyzed Preparation of Benzo[3,4]indolo[1,2-b]isoquinoline-8-ones and Photoluminescence Exploration DOI
Yiwen Hua, Ziyan Chen,

Hanying Diao

et al.

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(15), P. 9614 - 9621

Published: July 13, 2020

A facile synthesis of benzo[3,4]indolo[1,2-b]isoquinolin-8-ones is described. Under copper catalysis, the reaction proceeds with a high efficiency and broad scope. deuteration experiment shows that KIE value 2.85. From results on mechanism studies, copper-catalyzed C–H activation, intramolecular cis-addition alkynes, reductive elimination are involved. Moreover, this skeleton indeed new fluorophore, its photophysical properties also investigated.

Language: Английский

Citations

19
Recent advances of versatile reagents as controllable building blocks in organic synthesis DOI
Shaomin Chen, Luigi Vaccaro, Yanlong Gu

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(2), P. 109152 - 109152

Published: Sept. 27, 2023

Language: Английский

Citations

7
Rh-catalysed divergent synthesis of polysubstituted pyrroles from α,β-unsaturated ketones via selective single or double insertion of isocyanides DOI
Takuya Shimbayashi,

Taiyou Ishige,

Ken‐ichi Fujita

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(22), P. 5559 - 5567

Published: Jan. 1, 2023

A novel divergent synthetic method for polysubstituted pyrroles from isocyanides and α,β-unsaturated ketones in the presence of a rhodium catalyst bis(pinacolato)diboron (B 2 pin ) is described here.

Language: Английский

Citations

6