Electrochemical Rhodium-Catalyzed C–H Cyclodimerization of Alkynes to Access Diverse Functionalized Naphthalenes: Involvement of RhIV/V and RhI Dual Catalysis DOI

Ziyi Guo,

Junjie Zhang, Jitan Zhang

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(42), P. 7784 - 7789

Published: Oct. 17, 2022

The first electrochemical rhodium-catalyzed C-H cyclodimerization of alkynes for the direct construction functionalized naphthalenes was reported. practicality and synthetic value this strategy were demonstrated by readily accessible scale-up synthesis transformation products. Detailed mechanistic studies evidenced that electricity played an important role during disproportionation (ECD) process to generate maintain catalytically active RhIV/V RhI species, which conducted activation.

Language: Английский

Electrochemical rhodium catalysed alkyne annulation with pyrazoles through anodic oxidation – a metal oxidant/additive free methodology DOI Creative Commons

Subban Kathiravan,

Prasad Anaspure

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(9), P. 2024 - 2033

Published: Jan. 1, 2023

A rhodium( iii ) catalysed electrochemical C–H annulation of alkynes with pyrazole without using metal oxidants/additives is reported.

Language: Английский

Citations

4
High Selectivity in Csp2–Csp2 versus Csp3–O Reductive Elimination from Cycloplatinated(IV) Complexes DOI
Marzieh Dadkhah Aseman,

Susan Kiyavash

Inorganic Chemistry, Journal Year: 2024, Volume and Issue: 63(27), P. 12475 - 12484

Published: June 22, 2024

The cycloplatinated(IV) complexes trans-[Pt(p-MeC6H4)(C∧N)(OAc)2(H2O)] (C∧N = benzo[h]quinolate, bhq, 2a, and 2-phenylpyridinate, ppy, 2b) were prepared by reacting the corresponding [Pt(p-MeC6H4)(C∧N)(SMe2)] precursors with PhI(OAc)2 through an oxidative addition (OA) reaction. Thermolysis of 2a at 65 °C generates cis-[Pt(κ1N-10-(p-MeC6H4)-bhq)(OAc)2(H2O)], 3a, which is product a Csp2Ar–Csp2bhq reductive elimination (RE). observed coupling reaction significantly different from previously reported analogous thermolysis trans-[PtMe(C∧N)(OAc)2(H2O)] 2c, 2d) that selectively releases Me–OAc (C–O RE). density functional theory (DFT) calculations experimental observations reveal occurs dissociation coordinated water ligand. This in turn followed concomitant bond forming breaking process via three-center ring transition state, contrast to Csp3Me–OAc coupling, had taken place outer sphere SN2 type RE methyl complexes.

Language: Английский

Citations

1
Ruthenaelectro-Catalyzed C–H Phosphorylation: ortho to para Position-Selectivity Switch DOI Creative Commons

Xue‐Ya Gou,

João C. A. Oliveira, Shan Chen

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 29, 2024

The position-selective C-H bond activation of arenes has long been a challenging topic. Herein, we report an expedient ruthenium-electrocatalyzed site-selective

Language: Английский

Citations

1
Synthesis of Indole-Fused Six-, Seven-, or Eight-Membered N,O-Heterocycles via Rhodium-Catalyzed NH-Indole-Directed C–H Acetoxylation/Hydrolysis/Annulation DOI

Guoshuai Pan,

Leipeng Lu,

Weihui Zhuang

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(23), P. 16753 - 16763

Published: Nov. 10, 2021

We report herein the facile synthesis of indole-fused six-, seven-, or eight-membered N,O-heterocycles through rhodium-catalyzed C–H acetoxylation/hydrolysis/annulation. The notable features this method include acetoxylation using NH-indole as intrinsic directing group, high functional group compatibility, and construction medium-sized rings.

Language: Английский

Citations

9
Electrochemical Rhodium-Catalyzed C–H Cyclodimerization of Alkynes to Access Diverse Functionalized Naphthalenes: Involvement of RhIV/V and RhI Dual Catalysis DOI

Ziyi Guo,

Junjie Zhang, Jitan Zhang

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(42), P. 7784 - 7789

Published: Oct. 17, 2022

The first electrochemical rhodium-catalyzed C-H cyclodimerization of alkynes for the direct construction functionalized naphthalenes was reported. practicality and synthetic value this strategy were demonstrated by readily accessible scale-up synthesis transformation products. Detailed mechanistic studies evidenced that electricity played an important role during disproportionation (ECD) process to generate maintain catalytically active RhIV/V RhI species, which conducted activation.

Language: Английский

Citations

6