TfOH-Catalyzed Regioselective S–H Insertion of Cyclic Thioamide Derivatives with Diazo Compounds at Room Temperature DOI
Chunyan Li, Rui Wang, Huang Li

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(7), P. 4452 - 4457

Published: March 28, 2023

We have developed a method for highly regioselective S–H bond insertion reactions of various diazo compounds and cyclic thioamide derivatives at room temperature. These provide straightforward access to alkylated benzimidazoles, benzothiazoles, benzoxazoles. This mild uses readily available TfOH as catalyst features broad substrate scope, good functional group tolerance, excellent yields, high regioselectivities.

Language: Английский

Chiral phosphoric acid-catalyzed atroposelective oxidative coupling of carbazoles DOI
Lu Qian,

Minjie Bi,

Yong‐Bin Wang

et al.

Science China Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 14, 2025

Language: Английский

Citations

0
A combined experimental and computational study reveals a crossover between conventional cross-coupling and carbene insertion pathways in a Pd catalyzed C(sp2)–H insertion DOI Creative Commons

Arushi Tyagi,

Kritika Gaur,

Anubhav Goswami

et al.

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Computational (DFT and DLPNO-CCSD(T)) calculations along with experimental tools (deuterium labelling, kinetic studies using VTNA, ESI-HRMS UV) are used to probe the mechanism of a Pd(ii)-catalyzed enantioselective carbene insertion into C(sp2)-H indole. Using deuterium labelling studies, we demonstrate intermediacy metal-hydride species, which contrasts mechanistic routes for other transition metals (Rh, Fe, Au, Cu, etc.). Our VTNA study reveals order be one in both diazo indole, microkinetic modelling aligns well computationally predicted mechanism. The is further supported by detection most stable intermediate catalytic cycle ESI-HRMS. An investigation origin stereoselectivity DLPNO-CCSD(T) presents new paradigm, wherein stereocontrol arises during formation Pd itself as opposed proton transfer steps found all metal catalysts.

Language: Английский

Citations

0
Transition Metal‐Catalyzed Direct Functionalization of Carbazoles DOI
Vikash Kumar,

S. Sudharsan,

Lusina Mantry

et al.

The Chemical Record, Journal Year: 2025, Volume and Issue: unknown

Published: April 29, 2025

Abstract Carbazoles are an important class of nitrogen‐containing heterocycles found in diverse natural products, bioactive molecules, and functional materials. Their broader applications have driven extensive research into their synthesis functionalization. Among various approaches, transition metal‐catalyzed C−H activation has emerged as a powerful tool for direct functionalization, offering regioselectivity, efficiency, sustainability. This review comprehensively summarizes advancements functionalization carbazoles. Various catalytic systems employing palladium, ruthenium, rhodium, nickel, cobalt, copper, iron enabled alkylation, alkenylation, acylation, arylation, alkynylation, heteroatom incorporation These methodologies late‐stage diversification opened avenues accessing structurally complex carbazole derivatives with tailored properties. The aims to provide comprehensive guide researchers exploring via activation, highlighting key mechanistic insights, scope, emerging trends this field.

Language: Английский

Citations

0
Catalyst-controlled site-selective N–H and C3-arylation of carbazole via carbene transfer reactions DOI
Sourav Sekhar Bera, Srishti Ballabh Bahukhandi, Claire Empel

et al.

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(50), P. 6193 - 6196

Published: Jan. 1, 2021

A site-selective direct arylation reaction of carbazole and other N-heterocycles with diazo-naphthalen-2(1H)-ones has been developed.

Language: Английский

Citations

21
TfOH-Catalyzed Regioselective S–H Insertion of Cyclic Thioamide Derivatives with Diazo Compounds at Room Temperature DOI
Chunyan Li, Rui Wang, Huang Li

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(7), P. 4452 - 4457

Published: March 28, 2023

We have developed a method for highly regioselective S–H bond insertion reactions of various diazo compounds and cyclic thioamide derivatives at room temperature. These provide straightforward access to alkylated benzimidazoles, benzothiazoles, benzoxazoles. This mild uses readily available TfOH as catalyst features broad substrate scope, good functional group tolerance, excellent yields, high regioselectivities.

Language: Английский

Citations

8