Electrophile-Controlled Regiodivergent Palladium-Catalyzed Imidoylative Spirocyclization of Cyclic Alkenes DOI
Shumin Ding,

Yue Pu,

Jiao Lin

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(9), P. 1908 - 1913

Published: Feb. 26, 2024

An intermolecular controllable Pd-catalyzed spirocyclization of isocyano cycloalkenes has been developed, offering efficient and selective approaches toward spirocyclic hydropyrrole scaffolds. 2-Azaspiro-1,7-dienes could be obtained through a "chain-walking" process with aryl/vinyl iodides as electrophiles, while the normal Heck product 2-azaspiro-1,6-dienes were selectively generated when aryl triflates used coupling partner isocyanides. Mechanistic studies suggested that counteranion Pd(II) intermediate played crucial role in regioselectivity control. Dihydropyrrole-fused 5,6,7-membered spirocycles switchably accessed under mild conditions wide functional group tolerance.

Language: Английский

C–H functionalization enabled by multiple isocyanides DOI
Mingchun Gao, Shaohang Lu, Bin Xu

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

This review outlines in detail strategies for state-of-the-art synthetic routes and demonstrates various interactions from the synergistic combination of C–H functionalization with multiple isocyanides to establish complicated reactions.

Language: Английский

Citations

5
[1,2]‐Phospha‐Brook Rearrangement‐Initiated Palladium‐Catalyzed Cyclization Reaction of Isocyanides and o‐Bromobenzaldehydes: Access to 2H‐Isoindole‐1‐carboxamides and 2H‐Isoindole‐1‐carbonitriles DOI Open Access

Binbin Wang,

Qiushan Gao,

Huanfeng Jiang

et al.

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 20, 2024

Comprehensive Summary Herein, a [1,2]‐phospha‐Brook rearrangement‐initiated palladium‐catalyzed cyclization reaction for base‐controlled selective synthesis of 2 H ‐isoindole‐1‐carboxamide and ‐isoindole‐1‐carbonitrile derivatives has been described. This strategy features double isocyanide insertion, efficient bond combinations, simple operation conditions. Mechanistic studies show that the rearrangement is key step in this reaction. protocol offers novel concise ‐isoindole derivatives.

Language: Английский

Citations

2
Taming the Selective C−H Bond Activation through 1,5‐Palladium Migration DOI

Yaru Fang,

Mingruo Ding,

Xueliang Huang

et al.

ChemCatChem, Journal Year: 2023, Volume and Issue: 16(5)

Published: Nov. 29, 2023

Abstract “Through space” metal/hydrogen shift constitutes one of the efficient elementary step in organometallic chemistry to achieve selective remote C−H bond functionalization. Compared with relatively extensive exploration on 1,4‐palladium migration, processes corresponding 1,5‐palladium translocation are far less explored. Based our understanding related research areas, we summarized advances achieved activation through a key migration this minireview. The background, reaction scope, and more importantly, mechanistic rationale each transformation was discussed. We hope by reading minireview, could get general perspective direct via 1,5‐palladium/hydrogen shift, understand why such process is common when compared going 1,4‐palladium/hydrogen eventually be inspired develop practical ways for synthesis valuable molecules, which not prepared easily other traditional approaches.

Language: Английский

Citations

4
Electrophile-Controlled Regiodivergent Palladium-Catalyzed Imidoylative Spirocyclization of Cyclic Alkenes DOI
Shumin Ding,

Yue Pu,

Jiao Lin

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(9), P. 1908 - 1913

Published: Feb. 26, 2024

An intermolecular controllable Pd-catalyzed spirocyclization of isocyano cycloalkenes has been developed, offering efficient and selective approaches toward spirocyclic hydropyrrole scaffolds. 2-Azaspiro-1,7-dienes could be obtained through a "chain-walking" process with aryl/vinyl iodides as electrophiles, while the normal Heck product 2-azaspiro-1,6-dienes were selectively generated when aryl triflates used coupling partner isocyanides. Mechanistic studies suggested that counteranion Pd(II) intermediate played crucial role in regioselectivity control. Dihydropyrrole-fused 5,6,7-membered spirocycles switchably accessed under mild conditions wide functional group tolerance.

Language: Английский

Citations

1