Reductive cleavage of the N–O bond: elemental sulfur-mediated conversion of N-alkoxyamides to amides

2019 ◽  
Vol 6 (3) ◽  
pp. 347-351 ◽  
Author(s):  
Senlin Wang ◽  
Xue Zhao ◽  
Daisy Zhang-Negrerie ◽  
Yunfei Du
Keyword(s):  
Elemental Sulfur ◽  
Reductive Cleavage ◽  
Metal Free

By treating with elemental sulfur in the presence of DABCO in DMSO, a variety of N-alkoxyamides were readily converted to amides in satisfactory to excellent yields via a metal-free reductive cleavage of the N–O bond.

scholarly journals Metal-Free Reductive Cleavage of CN and SN Bonds by Photoactivated Electron Transfer from a Neutral Organic Donor

2013 ◽  
Vol 126 (2) ◽  
pp. 484-488 ◽  
Author(s):  
Steven O'Sullivan ◽  
Eswararao Doni ◽  
Tell Tuttle ◽  
John A. Murphy
Keyword(s):  
Electron Transfer ◽  
Reductive Cleavage ◽  
Metal Free

scholarly journals Metal-free direct thiocarbamation of imidazopyridines with carbamoyl chloride and elemental sulfur

RSC Advances ◽  
2017 ◽  
Vol 7 (85) ◽  
pp. 54013-54016 ◽  
Author(s):  
Jian-Chao Deng ◽  
Shi-Bin Zhuang ◽  
Quan-Zhu Liu ◽  
Zi-Wei Lin ◽  
Yu-Liang Su ◽  
...  
Keyword(s):  
Elemental Sulfur ◽  
Metal Free

Metal-free direct thiocarbamation of imidazopyridines using elemental sulfur.

Facile Access to Triazole-Fused 3,1-Benzoxazines Enabled by Metal-Free Base-Promoted Intramolecular C–O Coupling

Synthesis ◽  
2021 ◽  
Author(s):  
Yury N. Kotovshchikov ◽  
Stepan S. Tatevosyan ◽  
Gennadij V. Latyshev ◽  
Nikolay V. Lukashev ◽  
Irina P. Beletskaya
Keyword(s):  
Transition Metal ◽  
Functional Group ◽  
Cost Effective ◽  
Reductive Cleavage ◽  
Effective Procedure ◽  
Free Base ◽  
Metal Free ◽  
Fused Heterocycles ◽  
Convenient Approach

AbstractA convenient approach to assemble 1,2,3-triazole-fused 4H-3,1-benzoxazines has been developed. Diverse alcohol-tethered 5-iodotriazoles, readily accessible by a modified protocol of Cu-catalyzed (3+2)-cycloaddition, were utilized as precursors of the target fused heterocycles. The intramolecular C–O coupling proceeded efficiently under base-mediated transition-metal-free conditions, furnishing cyclization products in yields up to 96%. Suppression of the competing reductive cleavage of the C–I bond was achieved by the use of Na2CO3 in acetonitrile at 100 °C. This practical and cost-effective procedure features a broad substrate scope and valuable functional group tolerance.

Metal-Free Dehydrogenative Double C–H Sulfuration To Access Thieno[2,3-b]indoles Using Elemental Sulfur

2019 ◽  
Vol 84 (20) ◽  
pp. 12946-12959 ◽  
Author(s):  
Jianming Liu ◽  
Yanyan Zhang ◽  
Yuanyuan Yue ◽  
Zhixian Wang ◽  
Huibin Shao ◽  
...  
Keyword(s):  
Elemental Sulfur ◽  
Metal Free

Synthesis of α-Keto Thioamides by Metal-Free C═C Bond Cleavage in Enaminones Using Elemental Sulfur

2018 ◽  
Vol 84 (2) ◽  
pp. 1064-1069 ◽  
Author(s):  
Lu Gan ◽  
Yong Gao ◽  
Li Wei ◽  
Jie-Ping Wan
Keyword(s):  
Elemental Sulfur ◽  
Bond Cleavage ◽  
Metal Free

Metal-Free Aminothiation of Alkynes: Three-Component Tandem Annulation toward Indolizine Thiones from 2-Alkylpyridines, Ynals, and Elemental Sulfur

2019 ◽  
Vol 84 (19) ◽  
pp. 12639-12647 ◽  
Author(s):  
Zhengwang Chen ◽  
Pei Liang ◽  
Fan Xu ◽  
Zhen Deng ◽  
Lipeng Long ◽  
...  
Keyword(s):  
Elemental Sulfur ◽  
Metal Free

Hydride-catalyzed selectively reductive cleavage of unactivated tertiary amides using hydrosilane

2019 ◽  
Vol 9 (15) ◽  
pp. 3874-3878 ◽  
Author(s):  
Wubing Yao ◽  
Rongrong Li ◽  
Jianguo Yang ◽  
Feiyue Hao
Keyword(s):  
Transition Metal ◽  
Reductive Cleavage ◽  
Metal Free ◽  
Free Process ◽  
Tertiary Amides ◽  
Current Systems

The first hydride-catalyzed reductive cleavage of tertiary amides using the hydrosilane as reducing reagent has been developed. This transition-metal-free process may offer a versatile alternative to current systems for the selective reductive cleavage of amides.

scholarly journals Et3N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties

2020 ◽  
Vol 16 ◽  
pp. 1740-1753 ◽  
Author(s):  
Dharmender Singh ◽  
Vipin Kumar ◽  
Virender Singh
Keyword(s):  
Transition Metal ◽  
Elemental Sulfur ◽  
Photophysical Properties ◽  
Quantum Yields ◽  
One Pot ◽  
Light Emitting ◽  
Metal Free ◽  
One Pot Synthesis ◽  
Synthetic Strategy ◽  
Reaction Proceeds

A robust transition-metal-free strategy is presented to access novel β-carboline-tethered benzothiophenone derivatives from 1(3)-formyl-β-carbolines using elemental sulfur activated by Et3N/DMSO. This expeditious catalyst-free reaction proceeds through the formation of β-carboline-based 2-nitrochalcones followed by an incorporation of sulfur to generate multifunctional β-carboline-linked benzothiophenones in good to excellent yields. The synthetic strategy could also be extended towards the synthesis of β-carboline-linked benzothiophenes. Moreover, the afforded products emerged as promising fluorophores and displayed excellent light-emitting properties with quantum yields (ΦF) up to 47%.

ChemInform Abstract: Metal-Free Reductive Cleavage of N-O Bonds in Weinreb Amides by an Organic Neutral Super-Electron Donor.

ChemInform ◽  
2008 ◽  
Vol 39 (52) ◽  
Author(s):  
Sylvain P. Y. Cutulic ◽  
John A. Murphy ◽  
Hardeep Farwaha ◽  
Sheng-Ze Zhou ◽  
Ewan Chrystal
Keyword(s):  
Electron Donor ◽  
Reductive Cleavage ◽  
Metal Free ◽  
Weinreb Amides
Sign in / Sign up

Export Citation Format

Share Document