N-heterocyclic carbene-catalyzed reassembling of dibenzyl ethers: facile access to α-hydroxy ketones DOI

Lei Ju,

Teng Wang, Xinhong Yu

et al.

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

Published: July 16, 2024

Abstract A novel one-pot cascade process of oxidation-initiated, N-heterocyclic carbene catalyzed, reintegration dibenzyl ethers has been developed for the first time. This protocol allows straightforward access to α-hydroxy ketones from ethers. It is noteworthy that present method attempt synthesize benzoin ether.

Language: Английский

Alkyl radicals from diacyl peroxides: metal-/base-/additive-free photocatalytic alkylation of N-heteroaromatics DOI

Fukun Cheng,

Lulu Fan, Qi‐Yan Lv

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(20), P. 7971 - 7977

Published: Jan. 1, 2023

Alkyl diacyl peroxides were demonstrated to be efficient alkylating reagents for the visible-light-induced 4CzIPN-catalyzed direct C–H alkylation of N -heteroaromatics.

Language: Английский

Citations

47

Decatungstate-photocatalyzed direct acylation of N-heterocycles with aldehydes DOI
Zhiyang Zhang,

Fukun Cheng,

Xinyu Ma

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(12), P. 7331 - 7336

Published: Jan. 1, 2024

A novel photocatalytic acylation strategy was developed harnessing tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer (HAT) photocatalyst to facilitate the direct coupling of aldehydes with N-heterocycles at ambient temperature.

Language: Английский

Citations

17

Photodecarboxylative C–H Alkylation of Azauracils with N-(Acyloxy)phthalimides DOI

Satya Prakash Panda,

Sudhir Kumar Hota,

Rupashri Dash

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(20), P. 3739 - 3744

Published: May 15, 2023

We disclose a transition-metal-free NaI/PPh3-mediated direct C-H alkylation of azauracils using N-(acyloxy)pthalimides (NHPIs) as readily available alkyl surrogates under visible light irradiation. Detailed mechanistic studies reveal formation photoactivated electron donor-acceptor (EDA) complex between NaI/PPh3, TMEDA, and NHPI ester establish the crucial role TMEDA in increasing activity photoredox system. The reaction demonstrates broad scope, scalability, appreciable functional group tolerance. A variety are shown to undergo by primary, secondary, tertiary esters mild conditions, furnishing desired products good excellent yields.

Language: Английский

Citations

38

Visible-Light-Induced C–H Cyanoalkylation of Azauracils with Cycloketone Oxime Esters via Catalytic EDA Complex DOI
Xiaolong Huang,

Dong‐Liang Zhang,

Qing Li

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(18), P. 3727 - 3732

Published: April 28, 2024

Photoexcitation electron donor-acceptor (EDA) complexes provide an effective approach to produce radicals under mild conditions, while the catalytic version of EDA complex photoactivation remains scarce. Herein, we report a visible-light-induced organophotocatalytic pathway for cyanoalkylation azauracils using inexpensive and readily available 1,4-diazabicyclo[2.2.2]octane (DABCO) as donor. This synthetic method exhibits exceptional compatibility with various functional groups presents 34 examples in high yields. The efficient offers environmentally friendly sustainable route toward enhancing structural diversity azauracils.

Language: Английский

Citations

11

Electrochemical C–H Alkylation of Azauracils Using N-(Acyloxy)phthalimides DOI

Rupashri Dash,

Satya Prakash Panda,

Kuldeep Singh Bhati

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(34), P. 7227 - 7232

Published: Aug. 20, 2024

We present an electrochemical alkylation of azauracils using N-(acyloxy)phthalimides (NHPI esters) as readily available alkyl radical progenitors under metal- and additive-free conditions. Several are shown to undergo with array NHPI esters (1°, 2°, 3°, sterically congested), providing the desired products in good excellent yields. This operationally simple method is robust, scalable, suitable for both batch flow setups.

Language: Английский

Citations

9

Metal-free direct C–H phosphonation of N-heterocycles with diphenylphosphine oxides under mild conditions DOI

Zhaonan Cai,

Yaping Han, Yuecheng Zhang

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(14), P. 5721 - 5726

Published: Jan. 1, 2023

Herein, metal-free phosphonation of N-heterocycles with diphenylphosphine oxides, promoted by 1,5-diazabicyclo[5,4,0]undec-5-ene utilizing air as a green oxidant in dimethyl carbonate an eco-friendly solvent at room temperature, is presented.

Language: Английский

Citations

17

Rose‐Bengal‐Photocatalyzed Cross‐Dehydrogenative Coupling Reactions under Visible Light DOI

Divyani P. Patel,

Satish K. Singh

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(8)

Published: Jan. 19, 2024

Abstract Over the past few years, organic chemistry has used dye rose bengal‘s ability to absorb visible light. In present‐day research, innovation of environmentally friendly processes for carbon‐carbon/carbon‐heteroatoms (Nitrogen, Oxygen, Sulphur, and Phosphorus) bond formation great importance. The photocatalyzed cross‐dehydrogenative coupling (CDC) reactions using bengal (RB) is a promising technique creating carbon‐carbon/carbon‐heteroatom bonds directly from readily available compounds. Our review focuses on current advancement in that uses bond‐making synthesize various important molecules via CDC reactions.

Language: Английский

Citations

6

Photoinduced arylation or alkylation of 1,2,4-triazine-3,5(2H,4H)-diones with hydrazines DOI

Youlu Pan,

Yingchen Zhu,

Shuangshuang Li

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(27), P. 3665 - 3668

Published: Jan. 1, 2024

An innovative and eco-friendly method has been developed for synthesizing 6-arylated or 6-alkylated 1,2,4-triazine-3,5(2 H ,4 )-diones, utilizing a photoinduced cross-dehydrogenative coupling reaction with hydrazines.

Language: Английский

Citations

6

Minisci‐Type Carbamoylation of Azauracils with Oxamic Acids DOI
Changduo Pan, Dongdong Chen,

Miao Zeng

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(7)

Published: Jan. 19, 2024

Abstract A Minisci‐type carbamoylation of azauracils was developed to afford 6‐carbamoyl in yields up 94 %. In this transformation, oxamic acids were employed as the carbamoyl radical sources under metal‐free conditions. It features high atom economy, good functional group compatibility and convenient operation.

Language: Английский

Citations

5

Photoinduced Metal‐/Additive‐Free Difluoromethylation of N‐Heteroaromatics DOI Open Access
Congjun Zhu, Yangyang Shen, Tao Guo

et al.

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

Published: Jan. 16, 2025

Comprehensive Summary Herein, we report a photo‐induced, metal‐/additive‐free protocol for the difluoromethylation of N ‐heteroaromatics with [bis(difluoroacetoxy)iodo]benzene as reagent. The affords difluoromethylated in moderate to good yield (up 91%). transformation is compatible wide range substrates and has tolerance towards various functional groups. Moreover, synthetic value this method further demonstrated by applications gram‐scale synthesis late‐stage functionalization biologically important molecules.

Language: Английский

Citations

0