Ir(I)‐Catalyzed C−H Glycosylation for Synthesis of 2‐Indolyl‐C‐Deoxyglycosides DOI
Changyue Yu,

Yichu Liu,

Xiong Xie

et al.

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(21), P. 4926 - 4931

Published: Aug. 31, 2021

Abstract The construction of 2‐deoxy‐ C ‐glycosides has gradually become a hotspot carbohydrate chemistry in recent years. In this work, we present an efficient, regioselective, stereoselective and widely applicable strategy for the synthesis 2‐indolyl‐ ‐deoxyglycosides via Ir(I)‐catalyzed, pyridine‐group‐directed C−H functionalization. This method exhibits high tolerance functional groups indoles protecting carbohydrates. Moreover, protocol good stereoselectivity mainly produces β ‐configuration products. Gram‐scale several practical transformations were conducted further applications. Meantime, also explored mechanism proposed catalytic cycle magnified image

Language: Английский

C–H activation DOI
Torben Rogge, Nikolaos Kaplaneris, Naoto Chatani

et al.

Nature Reviews Methods Primers, Journal Year: 2021, Volume and Issue: 1(1)

Published: June 17, 2021

Language: Английский

Citations

435
Transition-Metal-Catalyzed C–H Bond Activation for the Formation of C–C Bonds in Complex Molecules DOI Creative Commons
Jamie H. Docherty,

Thomas M. Lister,

Gillian McArthur

et al.

Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(12), P. 7692 - 7760

Published: May 10, 2023

Site-predictable and chemoselective C–H bond functionalization reactions offer synthetically powerful strategies for the step-economic diversification of both feedstock fine chemicals. Many transition-metal-catalyzed methods have emerged selective activation bonds. However, challenges regio- chemoselectivity with application to highly complex molecules bearing significant functional group density diversity. As molecular complexity increases within structures risks catalyst intolerance limited applicability grow number groups potentially Lewis basic heteroatoms. Given abundance bonds already diversified such as pharmaceuticals, natural products, materials, design selection reaction conditions tolerant catalysts has proved critical successful direct functionalization. such, innovations formation carbon–carbon been discovered developed overcome these limitations. This review highlights progress made metal-catalyzed C–C forming including alkylation, methylation, arylation, olefination targets.

Language: Английский

Citations

228
Tryptophan-specific modification and diversification of peptides and proteins DOI
S K Kundu, A. Bandyopadhyay, Rajib Sarkar

et al.

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

Published: Jan. 1, 2025

This review provides an account of the tryptophan-specific conjugation peptides and proteins its extensive application in imaging living cells, radiolabelling proteins, protein engineering, etc .

Language: Английский

Citations

2
Late‐Stage Peptide Macrocyclization by Palladium‐Catalyzed Site‐Selective C−H Olefination of Tryptophan DOI

Zengbing Bai,

Chuangxu Cai,

Wangjian Sheng

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(34), P. 14686 - 14692

Published: June 8, 2020

Transition-metal-catalyzed C-H activation has shown potential in the functionalization of peptides with expanded structural diversity. Herein, development late-stage peptide macrocyclization methods by palladium-catalyzed site-selective C(sp2 )-H olefination tryptophan residues at C2 and C4 positions is reported. This strategy utilizes backbone as endogenous directing groups provides access to macrocycles unique Trp-alkene crosslinks.

Language: Английский

Citations

71
Progress and perspectives on directing group-assisted palladium-catalysed C–H functionalisation of amino acids and peptides DOI
Sadegh Shabani, Yuezhou Wu, Hannah G. Ryan

et al.

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(16), P. 9278 - 9343

Published: Jan. 1, 2021

Peptide modifications can unlock a variety of compounds with structural diversity and abundant biological activity. In nature, peptide modifications, such as functionalisation at the side-chain position amino acids, are performed using post-translational modification enzymes or incorporation unnatural acids. However, accessing these remains challenge for organic chemists. During past decades, selective C-H activation/functionalisation has attracted considerable attention in synthetic chemistry pathway to modification. Various directing group strategies have been discovered that assist activation. particular, bidentate groups enable tuneable reversible coordination now recognised one most efficient methods site-selective activation numerous families compounds. Synthetic chemists harnessed β- γ-positions This method expanded an effective device late stage macrocyclisation total synthesis complex natural products. this review, we discuss various β-, γ-, δ-C(sp3)-H bond reactions acids formation C-X bonds aid their application late-stage

Language: Английский

Citations

65
Rh(III)-Catalyzed [5 + 1] Annulation of Indole-enaminones with Diazo Compounds To Form Highly Functionalized Carbazoles DOI
Zhidong Jiang, Jianhui Zhou, Haoran Zhu

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(11), P. 4406 - 4410

Published: May 21, 2021

A novel Rh(III)-catalyzed C–H activation/annulation cascade of indole-enaminones with diazo compounds was reported to construct diversely functionalized carbazole frameworks. The most notable characteristic is that this transformation could smoothly furnish a [5 + 1] cyclization product good excellent yields (up 95%), accompanied by the thorough removal acetyl and N,N-dimethyl groups two substrates from target products, rather than normally expected [4 2] products.

Language: Английский

Citations

51
Rhodium(III)-Catalyzed Dehydrogenative Annulation and Spirocyclization of 2-Arylindoles and 2-(1H-Pyrazol-1-yl)-1H-indoles with Maleimides: A Facile Access to Isogranulatimide Alkaloid Analogues DOI

Vikki N. Shinde,

Krishnan Rangan, Dalip Kumar

et al.

The Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 86(3), P. 2328 - 2338

Published: Jan. 12, 2021

A Rh(III)-catalyzed dehydrogenative annulation and spirocyclization of 2-arylindoles 2-(1H-pyrazol-1-yl)-1H-indole with maleimides is described. The cascade protocol provided highly functionalized benzo[a]pyrrolo[3,4-c]carbazole-1,3(2H,8H)-diones spiro[isoindolo[2,1-a]indole-6,3′-pyrrolidine]-2′,5′-diones in good to excellent. developed reaction methodology exhibited broad substrate scope functional group tolerance operationally simple scalable. Photophysical properties the annulated products were investigated. product showed high absorption emission values a large red-shift as compared that 2-phenylindole.

Language: Английский

Citations

44
Recent advances in transition-metal-catalyzed directed C–H alkenylation with maleimides DOI
Shuang‐Liang Liu, Changchun Ye, Xiaoge Wang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(24), P. 4837 - 4845

Published: Jan. 1, 2022

Transition-metal-catalyzed directed C-H alkenylation with maleimides has attracted much attention in recent years, as maleimide core moieties are present various natural products and pharmaceuticals. In addition, these derivatives can be readily modified into biologically important compounds including succinimides, pyrrolidines γ-lactams. The efficient chelation-assisted inert bond activation strategy provides straightforward access to a wide array of structurally diverse molecules containing units. This review describes the major progress mechanistic investigations on Heck-type reaction/cyclization organic until early 2022.

Language: Английский

Citations

32
Ruthenium(II)-Catalyzed C–H Activation of Chromones with Maleimides to Synthesize Succinimide/Maleimide-Containing Chromones DOI
Yan Zhou, Liang Hong,

Yaoguang Sheng

et al.

The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(14), P. 9230 - 9243

Published: June 24, 2020

An efficient route for the coupling of maleimides with chromones at C5-position has been developed under Ru(II) catalysis. It could provide 1,4-addition products and oxidative Heck-type by switching additives. Benzoic acid led to formation solvent-free conditions, silver acetate was promoted generation products. Various were suitable this transformation, affording desired good excellent yields in a short reaction time. To understand mechanism reaction, deuteration studies control experiments have performed.

Language: Английский

Citations

42
Bone Regeneration Using MMP-Cleavable Peptides-Based Hydrogels DOI Creative Commons

Weikai Chen,

Ziyang Zhou, Dagui Chen

et al.

Gels, Journal Year: 2021, Volume and Issue: 7(4), P. 199 - 199

Published: Nov. 5, 2021

Accumulating evidence has suggested the significant potential of chemically modified hydrogels in bone regeneration. Despite progress bioactive with different materials, structures and loading cargoes, desires from clinical applications have not been fully validated. Multiple biological behaviors are orchestrated precisely during regeneration process, including marrow mesenchymal stem cells (BMSCs) recruitment, osteogenic differentiation, matrix calcification well-organized remodeling. Since metalloproteinases play critical roles such metabolism processes as BMSC commitment, osteoblast survival, osteoclast activation microstructure remodeling, metalloproteinase (MMP) cleavable peptides-based could respond to various MMP levels and, thus, accelerate In this review, we focused on MMP-cleavable peptides, polymers, functional modification crosslinked reactions. Applications, perspectives limitations for were then discussed.

Language: Английский

Citations

34