Access to syn α‐Amino‐β‐Hydroxyesters by N‐H Insertion on O‐Protected α‐Diazo‐β‐Hydroxyesters. DOI Creative Commons

Thomas Defuentes,

Jérôme Lhoste, Catherine Gaulon‐Nourry

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 13, 2024

Abstract The N−H insertion reaction is a versatile method for creating C−N bonds under mild conditions, providing in particular an efficient access to both natural and non‐natural α‐amino acid derivatives. In this field, the direct on α‐diazo‐β‐hydroxyesters has not yet been investigated constitutes significant challenge, due competitive migration processes. We report herein first insertions O ‐protected α‐diazo‐β‐aryl‐β‐hydroxyesters, enabling synthesize wide range of α‐amino‐β‐hydroxyesters by tuning nature amine aryl substituent. Overall, 28 products have isolated, with moderate good yields most cases, diastereoisomeric ratios up 8.0 : 1 favor syn diastereoisomer.

Language: Английский

Copper-Catalyzed Sulfur Alkylation of Sulfenamides with N-Sulfonylhydrazones DOI

Yidan Han,

Yin Yuan,

Shutao Qi

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3906 - 3910

Published: April 29, 2024

Sulfilimines are valuable compounds in both organic synthesis and pharmaceuticals. In this study, we present a copper-catalyzed sulfur alkylation of sulfenamides with

Language: Английский

Citations

6
Regulating the coordination microenvironment of zinc single-atom catalysts to enhance intramolecular hydroamination performance DOI
Li Wang, Chao Lv,

Kecan Dou

et al.

Inorganic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(14), P. 4207 - 4218

Published: Jan. 1, 2024

The Zn–N 2 P site, engineered with optimal electron density, demonstrates superior performance and enhanced reaction kinetics in the intramolecular hydroamination of o -alkynylaniline, outperforming current heterogeneous transition metal catalysts.

Language: Английский

Citations

5
Biomass‐Derived Cu‐Catalyzed General C—X (X = C, N, O) Bond Formation: Carbenoid Insertion Reactions of C—H, N—H, O—H Bond and Late‐stage Functionalization of Drug Molecules† DOI Open Access

Fu‐Hua Qin,

Wenxuan Xue, Conghui Tang

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 7, 2025

Comprehensive Summary The development of sustainable and efficient catalytic systems for the formation C—C, C—N, C—O bonds is a fundamental goal in modern synthetic chemistry. We present biomass‐derived Cu/Chitosan‐800 catalyst that facilitates range carbenoid insertion reactions into C—H, N—H, O—H bonds. This demonstrates remarkable activity, enabling functionalization diverse substrates, including late‐stage modification drug molecules with up to 95% yield good recyclability. Our findings highlight catalyst's potential advancing environmentally friendly chemical transformations, offering promising tool pharmaceutical synthesis organic synthesis.

Language: Английский

Citations

0
Low-coordinated single-atom Cu and enhanced charge transfer from Cu-N to TiO2 on Cu1/CN/TiO2 for efficient Sonogashira cross-coupling DOI
Shuo Zhang, Chao Shang, Li Chen

et al.

Chem Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 101290 - 101290

Published: Feb. 1, 2025

Language: Английский

Citations

0
Photoinduced Diazo Carbene-Promoted C(sp3)–H Oxidative Cross-Coupling Reaction for α-Triazolation of Isochromans DOI
Xiao Tang, Jinhua Liu, Xiang Wu

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 17, 2025

A photocatalytic diazo triplet carbene-promoted C(sp3)–H oxidative coupling of isochromans and triazoles was developed in up to 83% yield at room temperature air. The radical-like carbenes were used as efficient HAT acceptors, the possible synergistic enabled unprecedented process with a high regioselectivity.

Language: Английский

Citations

0
Unique Coordination Structure of Mo Species on MSilicalite-1 Robustly Boosting the Reaction Activity of Oxidative Dehydrogenative Coupling of Alcohols with Aromatic Diamines DOI
Liqin Wu, Wenqian Fu, Jiteng Liu

et al.

Industrial & Engineering Chemistry Research, Journal Year: 2025, Volume and Issue: unknown

Published: March 26, 2025

Language: Английский

Citations

0
Visible Light Induced B–H Bond Insertion Reaction with Diazo Compounds DOI

Mingjun Yi,

Xiaoyu Wu, Liqun Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12583 - 12590

Published: Aug. 19, 2024

A protocol induced by visible light for the direct insertion of α-carbonyl carbenes into B–H bond amine-borane adducts has been developed under conditions that are free metal and photocatalyst. This approach provides a straightforward route to various organoboron compounds from diazo with moderate good yields. Mechanistic investigations reveal this photoinduced reaction proceeds through concerted carbene bond, generation α-diazo esters may be rate-determining step.

Language: Английский

Citations

2
Dealuminated H–Y zeolites generate, stabilize and catalytically insert carbenes from diazocarbonyl compounds DOI Creative Commons

Yongkun Zheng,

Miguel Espinosa, Marta Mon

et al.

Journal of Catalysis, Journal Year: 2024, Volume and Issue: 440, P. 115835 - 115835

Published: Nov. 8, 2024

Language: Английский

Citations

2
Synthesis of α-ketoamides via oxidative amidation of Diazo Compounds with O-benzoyl hydroxylamines as Nitrogen Source and Oxidant DOI
Wenwen Chen, Xinying Zhang, Xinyu Wang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(33), P. 6708 - 6712

Published: Jan. 1, 2024

An efficient method for the construction of an array α-ketoamides has been described from readily available O -benzoyl hydroxylamines and diazo compounds as starting materials by combined use CuI a catalyst H 2 oxygen source.

Language: Английский

Citations

1
Access to syn α‐Amino‐β‐Hydroxyesters by N‐H Insertion on O‐Protected α‐Diazo‐β‐Hydroxyesters. DOI Creative Commons

Thomas Defuentes,

Jérôme Lhoste, Catherine Gaulon‐Nourry

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 13, 2024

Abstract The N−H insertion reaction is a versatile method for creating C−N bonds under mild conditions, providing in particular an efficient access to both natural and non‐natural α‐amino acid derivatives. In this field, the direct on α‐diazo‐β‐hydroxyesters has not yet been investigated constitutes significant challenge, due competitive migration processes. We report herein first insertions O ‐protected α‐diazo‐β‐aryl‐β‐hydroxyesters, enabling synthesize wide range of α‐amino‐β‐hydroxyesters by tuning nature amine aryl substituent. Overall, 28 products have isolated, with moderate good yields most cases, diastereoisomeric ratios up 8.0 : 1 favor syn diastereoisomer.

Language: Английский

Citations

0