Copper-Catalyzed [2,3]-Sigmatropic Rearrangement of Azide–Ynamides via Selenium Ylides DOI

Chong‐Yang Shi,

Xuan Wang, Xin Liu

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 23, 2024

A copper-catalyzed [2,3]-sigmatropic rearrangement of azide-ynamides via selenium ylides is disclosed, which leads to the practical and divergent synthesis a variety tricyclic heterocycles bearing quaternary carbon stereocenter in generally moderate excellent yields. Significantly, this method represents first ylide based on alkynes an unprecedented α-imino copper carbenes.

Language: Английский

Copper-Catalyzed Intermolecular [2 + 2 + 2] Annulation of Diynes with Alkynes: Construction of Carbazoles DOI
Zhentao Zhang,

Chen Luo,

Zhiyong Yu

et al.

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

Published: Jan. 9, 2025

Transition-metal-catalyzed [2 + 2 2] annulation of alkynes is an efficient pathway for the synthesis aromatic compounds. However, most established methods require noble metal catalysts. Herein, we report a copper-catalyzed intermolecular diynes with through vinyl cation intermediates, enabling atom-economical preparation biologically important carbazole skeletons. The reaction shows good regioselectivity in aryl(alkyl)alkynes. Moreover, preliminary results have also been obtained related catalytic atroposelective transformation. This represents rare example non-noble-metal-catalyzed ynamides pathway.

Language: Английский

Citations

1
Asymmetric one-carbon ring expansion of diverse N-heterocycles via copper-catalyzed diyne cyclization DOI Creative Commons

Fu-Shuai Li,

Xiuyuan Zou,

Tian-Qi Hu

et al.

Science Advances, Journal Year: 2024, Volume and Issue: 10(41)

Published: Oct. 9, 2024

One-carbon ring expansion reaction of N-heterocycles has gained particular attention in the past decade because this method allows for conversion readily available into potentially useful complex ring-expanded N-heterocycles, which are inaccessible by traditional methods. However, catalytic asymmetric variant been rarely reported to date. Herein, we disclose an enantioselective one-carbon through chiral copper-catalyzed diyne cyclization, leading practical, atom-economic and divergent assembly array valuable bearing a quaternary stereocenter generally good excellent yields with enantioselectivities (up >99% ee). This protocol represents first example based on alkynes.

Language: Английский

Citations

4
Copper-catalyzed asymmetric cascade diyne cyclization/Meinwald rearrangement DOI

Ji‐Jia Zhou,

Li‐Gao Liu, Zhentao Zhang

et al.

Chinese Chemical Letters, Journal Year: 2025, Volume and Issue: unknown, P. 110870 - 110870

Published: Jan. 1, 2025

Language: Английский

Citations

0
Copper-Catalyzed Triyne Cyclization via Vinyl Cations DOI
Chen Luo,

Yan-Xin Zheng,

Sheng-Biao Ji

et al.

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

Published: March 27, 2025

Herein, we describe an efficient copper-catalyzed cyclization of triynes via vinyl cation intermediates. The reaction leads to the practical and atom-economical synthesis valuable polycyclic pyrroles by constructing three new rings in one step under mild conditions. proposed mechanism shows ordered regioselective alkynes. Moreover, possibility such asymmetric triyne also emerges.

Language: Английский

Citations

0
Asymmetric Büchner reaction and arene cyclopropanation via copper-catalyzed controllable cyclization of diynes DOI Creative Commons

Yan-Xin Zheng,

Li‐Gao Liu,

Tian-Qi Hu

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Oct. 25, 2024

The asymmetric Büchner reaction and related arene cyclopropanations represent one type of the powerful methods for enantioselective dearomatization. However, examples reactions via a non-diazo approach are quite scarce, cyclopropanation based on alkynes has not been reported. Herein, we disclose an by copper-catalyzed controllable cyclization N-propargyl ynamides vinyl cation intermediates, leading to chiral tricycle-fused cycloheptatrienes benzonorcaradienes in high yields enantioselectivities. Importantly, this protocol represents cations.

Language: Английский

Citations

3
Catalytic Epoxidation of Carbonyl Compounds via Carbonyl Ylides: from Racemic to Enantioselective DOI
Linjun Qi, Bo Zhou, Long‐Wu Ye

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(41)

Published: May 23, 2024

Transition metal-catalyzed epoxidation of carbonyl compounds through ylides represents a highly effective method for synthesizing diverse range valuable epoxides. This review offers an in-depth overview the latest developments in inter- and intramolecular reactions involving metal carbenes compounds, encompassing both racemic to enantioselective transformations. These catalytic epoxidations are reviewed by highlighting their product selectivity, diversity applicability, related mechanistic rationale is showcased where possible.

Language: Английский

Citations

1
Tandem asymmetric dearomatized functionalization reaction of phenols with Evans-ynamides enabled by divergent electrophiles DOI
Yingqi Zhang,

Gan-Lu Qian,

Yun Liu

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 13, 2024

Language: Английский

Citations

1
Copper-catalyzed intermolecular formal [4 + 1] annulation of 1,5-diynes with benzocyclobutenones DOI Creative Commons
Jiacheng Li,

Tian-Qi Hu,

Zhou Xu

et al.

Tetrahedron Chem, Journal Year: 2024, Volume and Issue: 12, P. 100090 - 100090

Published: Aug. 14, 2024

Language: Английский

Citations

0
Gold(I)-catalyzed intramolecular C(sp3)—H bond functionalization DOI

Rubén Miguélez,

Omar Arto,

Carlos Rodríguez‐Arias

et al.

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

Published: Aug. 16, 2024

Abstract The merger of two the most rapidly growing fields in catalysis, namely gold-catalysis and C–H activation/functionalization has resulted major breakthroughs, affording unprecedented transformations. This review covers relevant contributions this field during last 10 years, restricted to intramolecular functionalization C(sp3)–H bonds. 1 Introduction 2 Carbene/Vinylidene Insertion 3 [1,5]-H Shift 4 Gold-Stabilized Vinyl Cation Mediated 5 Summary Outlook

Language: Английский

Citations

0
Copper‐Catalyzed Dearomative Cyclization of Indolyl Ynamides for Synthesis of Pentacyclic Spiroindolines DOI
Miao Xu,

Jia‐Tian Jiang,

Haoxuan Dong

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 23, 2024

Abstract The dearomatization of indoles with ynamides is a convenient access towards polycyclic spiroindolines, which can be initiated by α‐ and β‐additions ynamides. Currently, the related β‐addition dearomative cyclization requires noble‐metal catalyst or stoichiometric oxidant. Herein, we report copper‐catalyzed aryl‐substituted indolyl through regioselective onto ynamides, providing pentacyclic spiroindolines in 81–97% yields >25:1 diastereoselectivities. Moreover, preliminary success has been obtained for catalytic enantioselective cyclization.

Language: Английский

Citations

0