Ring Expansion toward Fused Diazabicyclo[3.1.1]heptanes through Lewis Acid Catalyzed Highly Selective C−C/C−N Bond Cross‐Exchange Reaction between Bicyclobutanes and Diaziridines DOI
Heng-Xian He, Feng Wu, Xu Zhang

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 13, 2024

Abstract The synthesis of bicyclic scaffolds has garnered considerable interest in drug discovery because their ability to mimic benzene bioisosteres. Herein, we introduce a new approach that utilizes Lewis acid (Sc(OTf) 3 )‐catalyzed σ‐bond cross‐exchange reaction between the C−C bond bicyclobutanes and C−N diaziridines produce multifunctionalized medicinally interesting azabicyclo[3.1.1]heptane derivatives. proceeds well with different broad range aryl‐ as alkenyl‐, but also alkyl‐substituted (up 98 % yield). Conducting scale‐up experiment exploring synthetic transformations cycloadducts emphasized practical application synthesis. Furthermore, zinc‐based chiral catalytic system was developed for enantioselective version this 96 ee ).

Language: Английский

Ring Expansion toward Fused Diazabicyclo[3.1.1]heptanes through Lewis Acid Catalyzed Highly Selective C−C/C−N Bond Cross‐Exchange Reaction between Bicyclobutanes and Diaziridines DOI
Heng-Xian He, Feng Wu, Xu Zhang

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 13, 2024

Abstract The synthesis of bicyclic scaffolds has garnered considerable interest in drug discovery because their ability to mimic benzene bioisosteres. Herein, we introduce a new approach that utilizes Lewis acid (Sc(OTf) 3 )‐catalyzed σ‐bond cross‐exchange reaction between the C−C bond bicyclobutanes and C−N diaziridines produce multifunctionalized medicinally interesting azabicyclo[3.1.1]heptane derivatives. proceeds well with different broad range aryl‐ as alkenyl‐, but also alkyl‐substituted (up 98 % yield). Conducting scale‐up experiment exploring synthetic transformations cycloadducts emphasized practical application synthesis. Furthermore, zinc‐based chiral catalytic system was developed for enantioselective version this 96 ee ).

Language: Английский

Citations

11
Divergent Synthesis of Silacycles by Ligand-Controlled Rhodium-Catalyzed Annulation of (2-Hydrosilylaryl)acetylenes DOI

Kazuto Fuji,

Kyohei Kawashima, Toshifumi Mori

et al.

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

Published: Feb. 6, 2025

This study demonstrates the rhodium-catalyzed divergent synthesis of 5-, 5,6-, and 8-membered silacyclic compounds, such as benzosilole, silolosiline, disilocine, from (2-hydrosilylaryl)acetylenes. To achieve high product selectivity, intra- intermolecular reactions are controlled by tuning mono- bidentate phosphine ligands on rhodium catalyst precursor. Deuterium labeling experiments computational studies reveal that annulation reaction proceeds via hydride transfer to alkyne moiety.

Language: Английский

Citations

1
Recent Status, Key Strategies, and Challenging Prospects for Fast Charging Silicon-Based Anodes for Lithium-Ion Batteries DOI
Tiantian Wang, Zhoulu Wang, Haiying Li

et al.

Carbon, Journal Year: 2024, Volume and Issue: 230, P. 119615 - 119615

Published: Sept. 8, 2024

Language: Английский

Citations

9
Photo-induced ring-maintaining hydrosilylation of unactivated alkenes with hydrosilacyclobutanes DOI Creative Commons
Shaowei Chen,

Meiyun Gao,

Xiaoqian He

et al.

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: March 12, 2025

Abstract Increasing attention has been paid to silacyclobutanes because of their wide application in ring opening and extension reactions. However, the synthesis functionalized remains an unmet challenge limited functional group tolerance reactions with organometallic reagents chlorosilacyclobutanes. Herein, we report a conceptually different solution this end through visible-light-induced metal-free hydrosilylation unactivated alkenes hydrosilacyclobutanes. A range diverse groups including base-sensitive acid, alcohol ketones participated reaction smoothly. In particular, first dihydrosilacyclobutane provides facile access various alkyl monohydrosilacyclobutanes. Unsymmetrical dialkyl have also synthesized consecutive one pot. The mechanism study reveals that Lewis basic solvent could promote generation strained silyl radicals by direct light irradiation without redox-active photocatalyst thiol catalyst plays important role accelerating reaction.

Language: Английский

Citations

1
Double strain-release enables formal C–O/C–F and C–N/C–F ring-opening metathesis DOI Creative Commons

Yulei Zhu,

Jie Jia,

Xiangyu Song

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(34), P. 13800 - 13806

Published: Jan. 1, 2024

Metathesis reactions have been established as a powerful tool in organic synthesis. While great advances were achieved double-bond metathesis, like olefin metathesis and carbonyl single-bond has received less attention the past decade. Herein, we describe first C(sp

Language: Английский

Citations

6
Alkali Metal-Hydroxide-Catalyzed Mechanisms of Csp-H Silylation of Alkyne: A DFT Investigation DOI

Tiantian Feng,

Ying Lin,

Bin Chen

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(31), P. 6352 - 6361

Published: Jan. 1, 2024

MOH/MH-catalytic mechanisms for Csp–H silylation were investigated using DFT.

Language: Английский

Citations

3
Modular and Regioselective Synthesis of Eight-Membered Benzosilacycles Enabled by Ring Expansion of Silacyclobutanes with Aryl Halides and Alkynes DOI
Zhenzhen Guo, Jinxiang Ye, Yingying Zhang

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 7066 - 7078

Published: April 16, 2025

Language: Английский

Citations

0
Borane-Catalyzed Intermolecular Aryl Transfer between Hydrosilanes: Shifting the Equilibrium by Removal of a Gaseous Hydrosilane DOI

Jiong Zhang,

Ximei Tian,

Yaqiong Wang

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 21, 2024

The preparation of organosilanes is indeed far from trivial, despite their vast application. Herein, we report a straightforward and general hydrosilane iterative evolution system for the on-demand synthesis heteroleptic-substituted hydrosilanes. A series previously difficult-to-prepare hydrosilanes with two or three diverse substituents were readily obtained. Our process achieved just by using catalytic amount BH

Language: Английский

Citations

1
Ring Expansion toward Fused Diazabicyclo[3.1.1]heptanes through Lewis Acid Catalyzed Highly Selective C−C/C−N Bond Cross‐Exchange Reaction between Bicyclobutanes and Diaziridines DOI
Heng-Xian He, Feng Wu, Xu Zhang

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 13, 2024

Abstract The synthesis of bicyclic scaffolds has garnered considerable interest in drug discovery because their ability to mimic benzene bioisosteres. Herein, we introduce a new approach that utilizes Lewis acid (Sc(OTf) 3 )‐catalyzed σ‐bond cross‐exchange reaction between the C−C bond bicyclobutanes and C−N diaziridines produce multifunctionalized medicinally interesting azabicyclo[3.1.1]heptane derivatives. proceeds well with different broad range aryl‐ as alkenyl‐, but also alkyl‐substituted (up 98 % yield). Conducting scale‐up experiment exploring synthetic transformations cycloadducts emphasized practical application synthesis. Furthermore, zinc‐based chiral catalytic system was developed for enantioselective version this 96 ee ).

Language: Английский

Citations

0