Synthesis of Hexafluoroisopropyl Aryl Ethers via Dual Photoredox/Nickel-Catalyzed C–O Coupling DOI
Xu He, Yuyang Zhang,

Jia‐Yi Shou

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6782 - 6786

Published: July 31, 2024

Herein we report a photoredox/nickel-catalyzed cross-coupling of aryl bromides with 1,1,1,3,3,3-hexafluoroisopropanol for the construction hexafluoroisopropyl ethers. The mild reaction conditions employed allow applicability wide range and heteroaryl bromides. Late-stage functionalization preliminary mechanistic studies have been demonstrated.

Language: Английский

An Electron‐Deficient CpE Iridium(III) Catalyst: Synthesis, Characterization, and Application to Ether‐Directed C−H Amidation DOI

Eiki Tomita,

M. Kojima, Yuki Nagashima

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(21)

Published: March 15, 2023

The synthesis, characterization, and catalytic performance of an iridium(III) catalyst with electron-deficient cyclopentadienyl ligand ([CpE IrI2 ]2 ) are reported. [CpE was synthesized by complexation a precursor the CpE [Ir(cod)OAc]2 , followed oxidation, desilylation, removal COD ligand. enabled C-H amidation reactions assisted weakly coordinating ether directing group. Experimental mechanistic studies DFT calculations suggested that high is due to its nature, which accelerates both activation IrV -nitrenoid formation.

Language: Английский

Citations

6
Recent Trends in Group 9 Catalyzed C–H Borylation Reactions: Different Strategies To Control Site-, Regio-, and Stereoselectivity DOI
Lukas Veth,

Hanusch A. Grab,

Paweł Dydio

et al.

Synthesis, Journal Year: 2021, Volume and Issue: 54(15), P. 3482 - 3498

Published: Dec. 2, 2021

Abstract Organoboron compounds continue contributing substantially to advances in organic chemistry with their increasing role as both synthetic intermediates and target for medicinal chemistry. Particularly attractive methods synthesis are based on the direct borylation of C–H bonds available starting materials since no additional pre-functionalization steps required. However, due high abundance similar reactivity molecules, synthetically useful protocols demand sophisticated strategies achieve regio- stereoselectivity. For this purpose, selective transition-metal-based catalysts have been developed, group 9 centered being among most commonly utilized. Recently, a multitude diverse has developed push boundaries reactions respect enantioselectivity. Herein, we provide an overview approaches arenes, alkenes, alkanes focus recent literature. Lastly, outlook is given assess future potential field. 1 Introduction 1.1 Mechanistic Considerations 1.2 Selectivity Issues Borylation 1.3 Different Modes Action Employing Directing Group Strategies 1.4 Scope Aim Short Review 2 Trends Reactions 2.1 Photoinduced Catalysis 2.2 Transfer 2.3 Lewis Acid Mediated 2.4 Directed Metalation 2.5 Miscellaneous 2.6 Electrostatic Interactions 2.7 Hydrogen Bonding 3 Conclusion Outlook

Language: Английский

Citations

12
Substrate‐Rhodium Cooperativity in Photoinducedortho‐Alkynylation of Arenes DOI
Argha Saha, Animesh Ghosh, Srimanta Guin

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(42)

Published: Aug. 24, 2022

In the realm of metallaphotocatalytic C-H activation strategy, direct excitation transition metal which plays dual role light energy harnessing alongside performing bond breaking and forming is a rare phenomenon. this context we have developed first photo-induced Rh-catalyzed ortho-alkynylation under ambient conditions without requirement silver salt, photocatalyst (PC) or any engineered substrate catalyst. The transformation functions by specific cooperative effect six-membered rhodacycle photo-responsive species. catalytic system allows conjugation arenes with sp3 -rich pharmacophoric fragments. control experiments as well computational studies resolve mechanistic intricacies for transformation. An outer sphere electron transfer process from Rh to alkynyl radical operative present over more common oxidative addition 1,2-migratory insertion pathways.

Language: Английский

Citations

9
Rhodium(II)‐Catalyzed C(sp3)−H Diamination of Arylcyclobutanes DOI
Xinyu Liu, Zhifan Wang, Qiwei Wang

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(30)

Published: May 24, 2022

Activated by multiple consecutive oxidative radical-polar crossover and desaturation processes, the selective diamination of arylcyclobutanes, which is difficult to perform classical metallonitrene C-H insertion, was achieved in a short time rhodium(II) catalysis using N-fluorobenzenesulfonimide (NFSI) as oxidant nitrogen source.

Language: Английский

Citations

8
Synthesis of Hexafluoroisopropyl Aryl Ethers via Dual Photoredox/Nickel-Catalyzed C–O Coupling DOI
Xu He, Yuyang Zhang,

Jia‐Yi Shou

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6782 - 6786

Published: July 31, 2024

Herein we report a photoredox/nickel-catalyzed cross-coupling of aryl bromides with 1,1,1,3,3,3-hexafluoroisopropanol for the construction hexafluoroisopropyl ethers. The mild reaction conditions employed allow applicability wide range and heteroaryl bromides. Late-stage functionalization preliminary mechanistic studies have been demonstrated.

Language: Английский

Citations

1