Palladium-catalysed imidoylative spirocyclization of 3-(2-isocyanoethyl)indoles DOI
Shi Tang, Shumin Ding, Dan Li

et al.

Chemical Communications, Journal Year: 2021, Volume and Issue: 57(81), P. 10576 - 10579

Published: Jan. 1, 2021

A palladium-catalysed construction of spiroindolines through dearomative spirocyclization 3-(2-isocyanoethyl)indoles has been developed. 2'-Aryl-, vinyl-, and alkyl-substituted could be accessed under mild conditions with excellent functional group tolerance. C1-tethered oxindole- indole-spiroindoline bisheterocycles were generated in high yields via alkene/allene insertion an imidoylative cascade. Additionally, a tandem dearomatization two different indoles was realized N-(2-bromobenzoyl)indoles as the electrophilic coupling partner 3-(2-isocyanoethyl)indoles, affording polyindoline - spiroindoline bisheterocyclic scaffolds conveniently. Under catalysis Pd(OAc)2 spinol-derived phosphoramidite ligand, chiral successfully up to 95% yield 85% ee.

Language: Английский

Exploiting Remarkable Reactivities of Ynamides: Opportunities in Designing Catalytic Enantioselective Reactions DOI
Jian Luo,

Guo‐Shu Chen,

Shujie Chen

et al.

ACS Catalysis, Journal Year: 2020, Volume and Issue: 10(23), P. 13978 - 13992

Published: Nov. 17, 2020

Ynamides consisting of an electron-withdrawing group on the nitrogen atom have proven to be powerful and versatile building blocks that are involved in a variety useful chemical transformations. Nonetheless, their utilization asymmetric catalysis is still its infancy has only recently attracted attention synthetic organic community. The focus this review present overview exciting results achieved thus far field catalytic reactions ynamides with emphasis advantages, limitations, mechanisms, applications associated current approaches. In addition, personal outlook challenges limitations need overcome area also given at end.

Language: Английский

Citations

130
Transition metal-catalysed carbene- and nitrene transfer to carbon monoxide and isocyanides DOI Creative Commons
Thomas R. Roose, Daniël S. Verdoorn, Pieter Mampuys

et al.

Chemical Society Reviews, Journal Year: 2022, Volume and Issue: 51(14), P. 5842 - 5877

Published: Jan. 1, 2022

Transition metal-catalysed carbene- and nitrene transfer to the C1-building blocks carbon monoxide isocyanides provides heteroallenes (i.e. ketenes, isocyanates, ketenimines carbodiimides). These are versatile reactive compounds allowing in situ transformation towards numerous functional groups organic compounds, including heterocycles. Both one-pot tandem processes have been developed providing valuable synthetic methods for chemistry toolbox. This review discusses all known transition reactions of hereby obtained, with a special focus on general mechanistic considerations.

Language: Английский

Citations

52
Chiral Spirocyclic Phosphoric Acids and Their Growing Applications DOI
Xufeng Lin, Lei Wang,

Zhao Han

et al.

Chinese Journal of Chemistry, Journal Year: 2020, Volume and Issue: 39(4), P. 802 - 824

Published: Oct. 14, 2020

Chiral spirocyclic phosphoric acids (SPAs) are introduced in 2010 and have been versatile catalysts capable of promoting a wide range asymmetric organocatalytic reactions, such as multi-component Friedel–Crafts Pictet–Spengler Fischer indolizations, cycloaddition desymmetrization dearomatization conjugate addition reactions rearrangement etc. Moreover, diverse applications metal-organic cooperative catalysis, organic photoredox total synthesis, materials science molecular recognition beautifully illustrated. This account summarizes the past decade's advances this field highlights selected but not comprehensive significant achievements. What is most favorite original chemistry developed your research group? Developing SPINOL-phosphoric (SPAs), TM-SPINOL-phosphoric (SPAs 2.0) PCP-derived planar chiral (PPAs) for catalysis. important personality scientific research? Curiosity, optimism, self-confidence persistence. What's hobbies? book(s)? I enjoy cooking. My book Journey to West. Who influences you mostly life? mother. journal(s)? The journals publishing systematic work synthetic chemistry. Could please give us some advices on improving Chinese Journal Chemistry? Fast review, fast publication, promotion via new media.

Language: Английский

Citations

60
Catalytic Enantioselective Isocyanide‐Based Reactions: Beyond Passerini and Ugi Multicomponent Reactions DOI
Jian Luo,

Guo‐Shu Chen,

Shu‐Jie Chen

et al.

Chemistry - A European Journal, Journal Year: 2020, Volume and Issue: 27(22), P. 6598 - 6619

Published: Sept. 23, 2020

Abstract The development of catalytic enantioselective isocyanide‐based reactions is currently great interest because the resulting products are valuable in organic synthesis, pharmacological chemistry, and materials science. This review assembles comprehensively summarizes recent achievements this rapidly growing area according to reaction types. Special attention paid advantages, limitations, possible mechanisms, synthetic applications each reaction. In addition, a personal outlook on opportunities for further exploration given at end.

Language: Английский

Citations

55
Recent Advances in Palladium-Catalyzed Isocyanide Insertions DOI Creative Commons
Jurriën W. Collet, Thomas R. Roose,

Bram Weijers

et al.

Molecules, Journal Year: 2020, Volume and Issue: 25(21), P. 4906 - 4906

Published: Oct. 23, 2020

Isocyanides have long been known as versatile chemical reagents in organic synthesis. Their ambivalent nature also allows them to function a CO-substitute palladium-catalyzed cross couplings. Over the past decades, isocyanides emerged practical and C1 building blocks, whose inherent N-substitution for rapid incorporation of nitrogeneous fragments wide variety products. Recent developments palladium catalyzed isocyanide insertion reactions significantly expanded scope applicability these imidoylative cross-couplings. This review highlights advances made this field over eight years.

Language: Английский

Citations

53
Recent advances of chromone-based reactants in the catalytic asymmetric domino annulation reaction DOI
M. Zhang,

Yi Gong,

Wei Zhou

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(14), P. 3968 - 3989

Published: Jan. 1, 2021

Chiral polycyclic chromanones are important heterocyclic frameworks that constitute the core structures of many natural products and bioactive molecules.

Language: Английский

Citations

51
Radical addition/spirocyclization cascade of tryptamine-derived isocyanides with aryl boronic acids: efficient access to spiroindoline derivatives DOI
Shuai Jiang, Yuxin Huang, Xiaofeng Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(7), P. 1660 - 1668

Published: Jan. 1, 2023

An efficient Mn( iii )-promoted cascade reaction of tryptamine-derived isocyanides with arylboronic acids for accessing spiroindoline derivatives is described.

Language: Английский

Citations

18
Can easy chemistry produce complex, diverse, and novel molecules? DOI Creative Commons
Anna Tomberg, Jonas Boström

Drug Discovery Today, Journal Year: 2020, Volume and Issue: 25(12), P. 2174 - 2181

Published: Oct. 1, 2020

• An analysis of screening compounds made by different synthetic methods was conducted. The notion that simple reactions cannot produce high quality structures disproved. Easy chemistry can be a reliable and efficient strategy in medicinal projects. Innovative is necessity for the production new elaborate building blocks. Statements, such as 'you need to break free from amide-formations improve molecular properties' 'novel leads novel biology' are frequently encountered community. To verify whether truth lies preconceptions, we investigated complex, diverse, molecules 'easy' chemistry. By analyzing AstraZeneca collection, conclude novelty, diversity, complexity currently not compromised use most popular reaction, amide bond formation, mainly because recent steady increase unique amines available. allows speedy access broad chemical space, facilitating progress projects, opens possibility synthesis automation technologies (e.g. DNA-encoded libraries). Easy-to-make often perceived inferior compared with obtained through reaction schemes. This study evaluates depths this perception true.

Language: Английский

Citations

44
Palladium(II)-Catalyzed Cross-Coupling of Diazo Compounds and Isocyanides to Access Ketenimines DOI
Zhaohong Liu, Shanshan Cao, Jiayi Wu

et al.

ACS Catalysis, Journal Year: 2020, Volume and Issue: 10(21), P. 12881 - 12887

Published: Oct. 20, 2020

Diazo compounds and isocyanides are reactive functionalities valuable building blocks commonly utilized in organic synthesis. Their cross-coupling for the synthesis of useful isolable ketenimines remains an unsolved challenge synthetic chemistry. Herein, we report a general method preparation via palladium-catalyzed easily accessible diazo with isocyanides. The reaction benefits from use readily available starting materials, wide substrate scope, high functional group tolerance, yield products, resultant amenable to further functionalization. Experimental findings DFT calculations unambiguously corroborate initial formation Pd(II)–isocyanide complex as active catalytic species, which enables migratory insertion Pd(II)–carbene into isocyanide, evidence suggesting that oxidation state Pd(II) unchanged during reaction.

Language: Английский

Citations

44
Hydrogen‐Bonding‐Promoted Cascade Rearrangement Involving the Enlargement of Two Rings: Efficient Access to Polycyclic Quinoline Derivatives DOI
Wenbin Cao, Shijun Li, Mengmeng Xu

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(48), P. 21425 - 21430

Published: Aug. 15, 2020

An efficient cascade reaction of tryptamine-derived isocyanides with C,N-cyclic azomethine imines is described. The polycyclic pyrrolo[2,3-c]quinoline derivatives, which benefited from rearrangement process driven by hydrogen bonding, could be directly assembled in moderate to good yields (40-87 %) under metal-free and mild conditions. This transformation involved four new heterocyclic rings formations uniquely, ring opening indole as well expansion imine. Both experimental DFT studies provided guidance on the in-depth insight into pathways bonding was identified lower free energy barrier transition states. work constitutes a rare example isocyanide-based reactions, potentially powerful synthetic strategy for accessing analogues natural products.

Language: Английский

Citations

41