Transition‐metal‐free Synthesis of tetra‐substituted Vinyl Iodides by Cascade Sequential Reaction of α‐Keto Acids, 1‐Iodoalkynes, and Alkyl Halides DOI
Xiaobao Zeng,

Zhenfeng Cheng,

Yushan Xie

et al.

Chemistry - An Asian Journal, Journal Year: 2022, Volume and Issue: 18(2)

Published: Dec. 2, 2022

The cascade sequential reaction of α-keto acids, 1-iodoalkynes, and alkyl halides are reported herein to synthesize tetra-substituted vinyl iodides. It represents an efficient protocol access a diverse range iodides starting from simple materials in one-pot fashion, featuring mild conditions, ease operation, broad substrate scope.

Language: Английский

Rhodium-Catalyzed Asymmetric C–H Functionalization Reactions DOI
Chen‐Xu Liu,

Si‐Yong Yin,

Fangnuo Zhao

et al.

Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(16), P. 10079 - 10134

Published: Aug. 1, 2023

This review summarizes the advancements in rhodium-catalyzed asymmetric C–H functionalization reactions during last two decades. Parallel to rapidly developed palladium catalysis, rhodium catalysis has attracted extensive attention because of its unique reactivity and selectivity reactions. In recent years, Rh-catalyzed have been significantly many respects, including catalyst design, reaction development, mechanistic investigation, application synthesis complex functional molecules. presents an explicit outline catalysts ligands, mechanism, scope coupling reagents, applications.

Language: Английский

Citations

120
Organic Peroxides in Transition-Metal-Free Cyclization and Coupling Reactions (C–C) via Oxidative Transformation DOI Creative Commons
Amin Rezaeifard, Fatemeh Doraghi, Fatemeh Akbari

et al.

ACS Omega, Journal Year: 2025, Volume and Issue: unknown

Published: April 14, 2025

Transition-metal-free transformations are recognized as green and sustainable methods for constructing carbon-carbon bonds in organic synthesis. This review describes the application of six peroxides, including tert-butyl hydroperoxide (TBHP), di-tert-butyl peroxide (DTBP), peroxybenzoate (TBPB), benzoyl (BPO), dialauroyl (DLP), diguyl (DCP), C-C bond construction, highlighting selected examples mechanisms challenging transformations. Each section concludes with a detailed overview suitable reagents various coupling reactions strengths weaknesses reported works. work aims to inspire further innovations transition-metal-free oxidative transformations, promoting eco-friendly chemical processes paving way new peroxide-based synthesis methods.

Language: Английский

Citations

0
Ferrocene-based amides, amines and alcohols as a platform for the design and synthesis of redox-active hybrids: Synthesis, electrochemical and computational studies DOI

M. V. Kaverin,

Ludmila N. Telegina,

А. N. Rodionov

et al.

Journal of Molecular Structure, Journal Year: 2024, Volume and Issue: 1312, P. 138584 - 138584

Published: May 9, 2024

Language: Английский

Citations

3
Ru(ii)-catalyzed C–H alkynylation of ferrocenes with bromoalkynes directed by carboxamide groups DOI
Ruyuan Zhao, Jing Zhang, Ruihan Niu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(8), P. 2007 - 2012

Published: Jan. 1, 2023

Ru( ii )-catalyzed C–H alkynylation of ferrocene carboxamides with easily accessible bromoalkyne compounds is depicted.

Language: Английский

Citations

8
Construction of β‐Phenylalanine Derivatives through Pd‐Catalyzed, C(sp2)−H (ortho) Functionalization DOI

Urja Narang,

Prabhakar Singh, Srinivasarao Arulananda Babu

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(29)

Published: June 13, 2023

Abstract This paper describes the Pd(II)‐catalyzed, picolinamide‐directing‐group‐aided C(sp 2 )−H ( ortho ) functionalization of racemic and enantiopure β ‐phenylalanines 3‐amino‐3‐phenylpropanols (1,3‐amino alcohols). The functionalizations including arylation, bromination, iodination, alkoxylation were attempted. arylation reactions gave biaryl or terphenyl‐type ‐phenylalanine scaffolds, halogenation methoxylation C−H halogenated methoxylated ‐phenylalanines. Additionally, an ‐methyl substituted containing both remote 3 bonds was investigated. ‐Phenylalanine is arylated ‐amino acid motif present in various natural products, bioactive molecules, ‐peptides it a precursor to medicinally active compounds. Accordingly, this work contributes expansion library unnatural acid) derivatives through site‐selective functionalization.

Language: Английский

Citations

7
The Versatile and Strategic O-Carbamate Directed Metalation Group in the Synthesis of Aromatic Molecules: An Update DOI Creative Commons
Ross D. Jansen‐van Vuuren,

Susana Liu,

M. A. Jalil Miah

et al.

Chemical Reviews, Journal Year: 2024, Volume and Issue: 124(12), P. 7731 - 7828

Published: June 12, 2024

The aryl

Language: Английский

Citations

2
Synthesis of Ferrocene 1,3‐Derivatives by Distal C−H Activation** DOI

Princi Gupta,

Suchithra Madhavan, Manmohan Kapur

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(34)

Published: June 27, 2023

The third position of cyclopentadienyl ring a monosubstituted ferrocene has remained as an inaccessible chemical space for direct functionalization. Until recently, functionalizing the C(3)-position while bypassing predominantly active C(2)-position is most challenging task. Herein, we report distal C-H functionalization ferrocenes using easily removable directing group with precise site-selectivity, under PdII / mono-N-protected amino-acid ligand catalytic system. robust synthetic protocol leads to synthesis 1,3-derivatives broad scope in olefins ferrocenyl methylamine moderate good yields via highly strained appended 12-membered palladacycle intermediate.

Language: Английский

Citations

6
Catalytic Undirected Meta‐Selective C–H Borylation of Metallocenes DOI Creative Commons
Hao Zheng, Changhui Liu, Xiaoyu Wang

et al.

Advanced Science, Journal Year: 2023, Volume and Issue: 10(31)

Published: Aug. 26, 2023

Metallocenes are privileged backbones in the fields of synthetic chemistry, catalysis, polymer science, etc. Direct C-H functionalization is undoubtedly simplest approach for tuning properties metallocenes. However, owing to presence multiple identical C(sp2 )-H sites, this protocol often suffers from low reactivity and selectivity issues, especially regioselective synthesis 1,3-difunctionalized Herein, an efficient iridium-catalyzed meta-selective borylation metallocenes reported. With no need preinstalled directing groups, enables a rapid various boronic esters based on benzoferrocenes, ferrocenes, ruthenocene, related half sandwich complex. A broad range electron-deficient -rich functional groups all compatible with process. Notably, benzoferrocenes takes place exclusively at benzene ring, which likely ascribed shielding effect pentamethylcyclopentadiene. The utility further demonstrated by easy scalability gram quantities, conversion boron heteroatoms including N3 , SePh, OAc, as well diverse cross-coupling reactions.

Language: Английский

Citations

5
Ni‐Catalyzed/mediated C−X (X=N, O, S) Bond Formation Chelation‐Assisted by Bidentate Directing Groups DOI
Peng Xu, Shengxian Zhao

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(5)

Published: Jan. 29, 2024

Abstract Recently, transition‐metal‐catalyzed C−H functionalization has attracted significant attention due to its potential applications in different fields. Among metals, nickel is regarded as a more sustainable 3d‐transition metal, which been widely explored. Therefore, this review focuses on the recent advances field of nickel‐catalyzed assisted with bidentate directing groups (DGs) construct C−X (N, S, O) bond. The latest advancement catalysed bond are reviewed and covers literatures from 2015–2022. In addition, substrate scope limitations well partial mechanism discussed.

Language: Английский

Citations

1
Enantioselective synthesis of planar chiral ferrocenes via gold(I)-catalyzed hydroarylation of N-ferrocenyl propiolamides DOI Creative Commons
Qian Zhou,

Lulin Qiao,

An‐An Zhang

et al.

Green Synthesis and Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: March 1, 2024

Herein, we report an intramolecular 6-endo-dig cyclization of N-ferrocenyl propiolamides for the synthesis planar chiral ferrocenes enabled by gold(I)-catalyzed hydroarylation. By using this protocol, a variety ferrocenopyridin-2(1H)-ones were obtained in good yields and excellent enantioselectivities (up to 96% ee).

Language: Английский

Citations

1