Cp*Co(III)-catalyzed ortho-alkylation/alkenylation of anilides DOI
Yongqi Yu, Jiajia Yu, Ying Li

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A highly practical and efficient Cp*Co( iii )-catalyzed regioselective C–H alkylation/alkenylation of anilides with maleimides acrylates was developed, during which a weakly coordinating amide group functioned as the directing group.

Language: Английский

Cobalt(III)/Chiral Carboxylic Acid‐Catalyzed Enantioselective Synthesis of Benzothiadiazine‐1‐oxides via C−H Activation DOI
Yuuki Hirata,

Daichi Sekine,

Yoshimi Kato

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(28)

Published: May 2, 2022

Abstract Among sulfoximine derivatives containing a chiral sulfur center, benzothiadiazine‐1‐oxides are important for applications in medicinal chemistry. Here, we report that the combination of an achiral cobalt(III) catalyst and pseudo‐ C 2 ‐symmetric H 8 ‐binaphthyl carboxylic acid enables asymmetric synthesis from sulfoximines dioxazolones via enantioselective C−H bond cleavage. With optimized protocol, with several functional groups can be accessed high enantioselectivity.

Language: Английский

Citations

73
Cobalt-catalyzed atroposelective C−H activation/annulation to access N−N axially chiral frameworks DOI Creative Commons
Tong Li, Linlin Shi,

Xinhai Wang

et al.

Nature Communications, Journal Year: 2023, Volume and Issue: 14(1)

Published: Aug. 29, 2023

The N-N atropisomer, as an important and intriguing chiral system, was widely present in natural products, pharmaceutical lead compounds, advanced material skeletons. anisotropic structural characteristics caused by its special axial rotation have always been one of the challenges that chemists strive to overcome. Herein, we report efficient method for enantioselective synthesis axially frameworks via a cobalt-catalyzed atroposelective C-H activation/annulation process. reaction proceeds under mild conditions using Co(OAc)2·4H2O catalyst with salicyl-oxazoline (Salox) ligand O2 oxidant, affording variety products high yields enantioselectivities. This protocol provides approach facile construction atropisomers further expands range derivatives. Additionally, electrocatalysis, desired were also successfully achieved good excellent efficiencies

Language: Английский

Citations

52
Cobalt-Catalyzed Enantioselective C–H Annulation with Alkenes DOI
Dandan Yang, Xian Zhang, Xinghua Wang

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(7), P. 4250 - 4260

Published: March 13, 2023

Herein, we disclose an efficient cobalt-catalyzed enantioselective C–H activation and annulation of benzamides with alkenes. This transformation is facilitated via the commercially available cobalt(II) catalyst in presence easily prepared chiral salicyl-oxazoline (Salox) ligand, which provides facile access to (R) or (S) enantiomers dihydroisoquinolone derivatives. It noticeable that reaction proceeded efficiently within extremely short time from 10 30 min under mild conditions. A broad range alkenes bear various functional substituents have been shown good compatibility deliver targeted products high yields enantioselectivities (51 examples, up 98% yield 99% ee). The gram scale experiment removal directing group further demonstrate practicability this protocol potential industrial applications. Density theory calculations elucidate mechanism, spin-state change olefin insertion step accelerates subsequent C–N reductive elimination, identified as stereo-determining step. AIM analysis indicates π interactions are vital for controlling switching stereoselectivity.

Language: Английский

Citations

45
Synergistic surface activation during photocatalysis on perovskite derivative sites in heterojunction DOI

Yalin Yang,

Zheyan Chen, Hanlin Huang

et al.

Applied Catalysis B Environment and Energy, Journal Year: 2022, Volume and Issue: 323, P. 122146 - 122146

Published: Nov. 7, 2022

Language: Английский

Citations

40
Cobalt-catalyzed enantioselective C–H/N–H annulation of aryl sulfonamides with allenes or alkynes: facile access to C–N axially chiral sultams DOI Creative Commons

Xiao‐Ju Si,

Xiaofang Zhao, Jianli Wang

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(26), P. 7291 - 7303

Published: Jan. 1, 2023

Herein we report a cobalt-catalyzed enantioselective C-H/N-H annulation of aryl sulfonamides with allenes and alkynes, using either chemical or electrochemical oxidation. By O2 as the oxidant, proceeds efficiently low catalyst/ligand loading 5 mol% tolerates wide range allenes, including 2,3-butadienoate, allenylphosphonate, phenylallene, resulting in C-N axially chiral sultams high enantio-, regio-, position selectivities. The alkynes also exhibits excellent enantiocontrol (up to >99% ee) variety functional sulfonamides, internal terminal alkynes. Furthermore, oxidative is achieved simple undivided cell, demonstrating versatility robustness cobalt/Salox system. gram-scale synthesis asymmetric catalysis further highlight practical utility this method.

Language: Английский

Citations

36
Enantioselective C–H bond functionalization under Co(iii)-catalysis DOI

Bholanath Garai,

Abir Das,

Doppalapudi Vineet Kumar

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(25), P. 3354 - 3369

Published: Jan. 1, 2024

Enantioselective C–H functionalization relies on 4d and 5d metals, but with their depletion, sustainable alternatives using 3d metals are crucial.

Language: Английский

Citations

13
(SCp)Rhodium‐Catalyzed Asymmetric Satoh–Miura Reaction for Building‐up Axial Chirality: Counteranion‐Directed Switching of Reaction Pathways DOI
Wenwen Zhang, Qiang Wang,

Suzhen Zhang

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 62(3)

Published: Nov. 16, 2022

Satoh-Miura reaction is an important method for extending π-systems by forging multi-substituted benzene rings via double aryl C-H activation and annulation with alkynes. However, the development of highly enantioselective remains rather challenging. Herein, we report asymmetric between 1-aryl benzo[h]isoquinolines internal alkynes enabled a SCpRh-catalyst. Judiciously choosing counteranion Rh-catalyst crucial desired reactivity over competitive formation azoniahelicenes. Detailed mechanistic studies support proposal counteranion-directed switching pathways in Rh-catalyzed activation.

Language: Английский

Citations

38
Recent progress in rare-earth metal-catalyzed sp2 and sp3 C–H functionalization to construct C–C and C–heteroelement bonds DOI
Kapileswar Seth

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(11), P. 3102 - 3141

Published: Jan. 1, 2022

The review presents rare-earth metal-catalyzed C(sp 2 /sp 3 )–H functionalization accessing C–C/C–heteroatom bonds and olefin (co)polymerization, highlighting substrate scope, mechanistic realization, origin of site-, enantio-/diastereo-selectivity.

Language: Английский

Citations

36
Organo-Se BTSAs-enabled performance: From racemic and asymmetric synthesis to click chemistry application DOI
Zhi Zhou,

Yuang Gu,

Liexin Wu

et al.

Chem, Journal Year: 2023, Volume and Issue: 9(11), P. 3335 - 3346

Published: Aug. 29, 2023

Language: Английский

Citations

19
Simultaneous construction of inherent and axial chirality by cobalt-catalyzed enantioselective C-H activation of calix[4]arenes DOI Creative Commons
Tong Li, Yanbo Zhang, Cong Du

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Sept. 3, 2024

Language: Английский

Citations

6