Stereoselective Synthesis of Conjugated Dienes via Aryl-to-Vinyl 1,4-Nickel Migration and Reductive Cross-Coupling DOI
Guohua Ren,

Haochen Li,

Yiming Duan

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 3, 2025

Selective functionalization of remote C-H bonds via metal/hydride shift and cross-coupling represents a powerful strategy in modern synthetic chemistry. Herein, we report highly efficient aryl-to-vinyl 1,4-nickel migration coupled with reductive for the stereoselective synthesis conjugated dienes. This tandem process proceeds under mild conditions, accommodates wide range substrates, achieves excellent regioselectivity Z/E stereoselectivity, offering valuable method constructing multisubstituted

Language: Английский

Recent Advances in Alkenyl sp2 C–H and C–F Bond Functionalizations: Scope, Mechanism, and Applications DOI
Mingzhu Lu, Jeffrey Goh, Manikantha Maraswami

et al.

Chemical Reviews, Journal Year: 2022, Volume and Issue: 122(24), P. 17479 - 17646

Published: Oct. 14, 2022

Alkenes and their derivatives are featured widely in a variety of natural products, pharmaceuticals, advanced materials. Significant efforts have been made toward the development new practical methods to access this important class compounds by selectively activating alkenyl C(sp2)–H bonds recent years. In comprehensive review, we describe state-of-the-art strategies for direct functionalization sp2 C–H C–F until June 2022. Moreover, metal-free, photoredox, electrochemical also covered. For clarity, review has divided into two parts; first part focuses on currently available using different alkene as starting materials, second describes bond easily accessible gem-difluoroalkenes material. This includes scope, limitations, mechanistic studies, stereoselective control (using directing groups well metal-migration strategies), applications complex molecule synthesis where appropriate. Overall, aims document considerable advancements, current status, emerging work critically summarizing contributions researchers working fascinating area is expected stimulate novel, innovative, broadly applicable functionalizations coming

Language: Английский

Citations

155
Catalytic asymmetric transformations of oxa- and azabicyclic alkenes DOI
Sundaravel Vivek Kumar, Andy Yen, Mark Lautens

et al.

Chemical Society Reviews, Journal Year: 2021, Volume and Issue: 50(5), P. 3013 - 3093

Published: Jan. 1, 2021

This review provides an overview of the fundamental concepts and recent developments in a wide range enantioselective transformations involving oxa- azabicyclic alkenes.

Language: Английский

Citations

61
Cobalt(III)-catalyzed asymmetric ring-opening of 7-oxabenzonorbornadienes via indole C–H functionalization DOI Creative Commons
Yang Zheng, Wenyun Zhang, Qing Gu

et al.

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

Published: Feb. 25, 2023

Abstract Asymmetric ring-opening of 7-oxabenzonorbornadienes is achieved via Co-catalyzed indole C–H functionalization. The utilization chiral Co-catalyst consisting a binaphthyl-derived trisubstituted cyclopentadienyl ligand resulted in high yields (up to 99%) and excellent enantioselectivity (>99% ee) for the target products with tolerance diverse functional groups. Opposite diastereoselectivities are obtained or Cp*CoI 2 CO. Combined experimental computational studies suggest β -oxygen elimination being selectivity-determining step reaction. Meanwhile, reactions 7-azabenzonorbornadiene could also be executed diastereodivergent manner.

Language: Английский

Citations

32
Synthesis of pyrazolone fused benzodiazepines via Rh(iii)-catalyzed [4 + 3] annulation of 1-phenylpyrazolidinones with propargyl alcohols DOI
Linghua Zhang,

Yuanshuang Xu,

Xiaopeng Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(16), P. 2284 - 2290

Published: Jan. 1, 2020

An efficient synthesis of pyrazolone fused benzodiazepines through an unprecedented regioselective [4 + 3] annulation 1-phenylpyrazolidinones with propargyl alcohols via Rh(iii)-catalyzed redox-neutral C–H/N–H/C–O bond activation is presented.

Language: Английский

Citations

57
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
Maleimides in Directing‐Group‐Controlled Transition‐Metal‐Catalyzed Selective C−H Alkylation DOI
Shuang‐Liang Liu, Yajun Shi, Cong Xue

et al.

European Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 2021(43), P. 5862 - 5879

Published: Oct. 20, 2021

Abstract Maleimides and succinimides are all vital scaffolds in biological fields various natural products. Maleimide derivatives have been extensively used as coupling partners for organic transformations, affording a broad array of important molecular architectures including succinimides. In the past decade, variety efficient chelation‐assisted strategies employed selective addition C−H bonds to maleimides giving succinimides, which also highly building blocks synthesis. This Review provides an overview research progress relating participated transition‐metal‐catalyzed group‐directed alkylation from 2012 2021. Significant advances this field were highlighted, diverse transition metal catalysts, substrates contained different directing groups, reaction mechanisms well synthetic applications systematically discussed. addition, limitations intractable issues need be solved future pointed out.

Language: Английский

Citations

41
Ruthenium-Catalyzed Site-Selective C–H Bond Activation/Annulation Cascade toward Dibenzoazepinone Skeletons DOI
Deepan Chowdhury, Suman Dana, Subhankar Maity

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(17), P. 6760 - 6764

Published: Aug. 14, 2020

A free amine-directed ruthenium(II)-catalyzed hydroarylation and concomitant regioselective transamidation cascade between 2-aminobiphenyls diversely substituted maleimides is reported, furnishing biologically relevant dibenzo[b,d]azepinone scaffolds in high yields. The protocol accommodates a range of functional groups showcases synthesis dibenzoazepinones bearing amino acid side chains through substrate design.

Language: Английский

Citations

37
Recent advances in directed sp2 C–H functionalization towards the synthesis of N-heterocycles and O-heterocycles DOI
Bhargav Desai,

Monak Patel,

Bharatkumar Z. Dholakiya

et al.

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(70), P. 8699 - 8725

Published: Jan. 1, 2021

Metal catalyzed C–H functionalization is a convenient and powerful strategy to construct various N,O-heterocycles. This review highlights the recent breakthroughs in synthesis of N,O-heterocycles via directed sp 2 functionalization.

Language: Английский

Citations

33
Photoredox catalysis in nickel-catalyzed C–H functionalization DOI Creative Commons
Lusina Mantry,

Rajaram Maayuri,

Vikash Kumar

et al.

Beilstein Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 17, P. 2209 - 2259

Published: Aug. 31, 2021

Catalytic C‒H functionalization has become a powerful strategy in organic synthesis due to the improved atom-, step- and resource economy comparison with cross-coupling or classical functional group transformations. Despite significant advances metal-catalyzed activations, recent developments field of metallaphotoredox catalysis enabled functionalizations unique reaction pathways under mild conditions. Given relative earth-abundance cost-effective nature, nickel catalysts for photoredox have received attention. In this review, we highlight nickel-catalyzed reactions range applications until summer 2021.

Language: Английский

Citations

30