Cu-Catalyzed Intermolecular γ-Site C–H Amination of Cyclohexenone Derivatives: The Benefit of Bifunctional Ligands DOI
Xin Zhao, Fang Yang,

Shao-Yu Zou

et al.

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(3), P. 1732 - 1741

Published: Jan. 18, 2022

Utilizing 1,10-phenanthroline-type bifunctional ligands, an efficient Cu-catalyzed intermolecular site-selective remote C–H amination using cyclohexenone derivatives and anilines was realized. The amide group installed on the ligand played a key role in stabilizing N-centered radical generated situ to realize C–N-directed formation. Meanwhile, useful catalytic system for γ-C–H p-aminophenols γ-aminated enones established. This economical practical approach oxygen as terminal oxidant mild environmentally friendly.

Language: Английский

Organoelectrocatalysis Enables Direct Cyclopropanation of Methylene Compounds DOI

Lianghua Jie,

Bin Guo, Jinshuai Song

et al.

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(5), P. 2343 - 2350

Published: Feb. 1, 2022

Cyclopropane is a prevalent structural unit in natural products and bioactive compounds. While the transition metal-catalyzed alkene cyclopropanation of functionalized compounds such as α-diazocarbonyl derivatives has been well established provides straightforward access to cyclopropanes, directly from more stable simpler methylene remained an unsolved challenge despite highly desirable benefits minimal prefunctionalization increased operational safety. Herein we report electrocatalytic strategy for active compounds, employing organic catalyst. The method shows broad substrate scope excellent scalability, requires no metal catalyst or external chemical oxidant, convenient several types cyclopropane-fused heterocyclic carbocyclic Mechanistic investigations suggest that reactions proceed through radical-polar crossover process form two new carbon-carbon bonds nascent cyclopropane ring.

Language: Английский

Citations

73

C(sp3)–H/C(sp3)–H Dehydrogenative Radical Coupling of Glycine Derivatives DOI
Jiayuan Wang,

Youwan Ye,

Tongzhi Sang

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(41), P. 7577 - 7582

Published: Oct. 10, 2022

Here we report a general C(sp3)–H/C(sp3)–H dehydrogenative coupling strategy for the preparation of various natural or unnatural amino acids from readily available glycine derivatives and hydrocarbons through combination SET HAT process.

Language: Английский

Citations

31

Electrochemical Annulation of Indole-Tethered Alkynes Enabling Synthesis of Exocyclic Alkenyl Tetrahydrocarbazoles DOI

Jingrui He,

Aiyao Liu, Yingjie Yu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 6962 - 6972

Published: May 22, 2023

An electrochemical sulfonylation-triggered cyclization reaction of indole-tethered terminal alkynes with sulfinates as sulfonyl sources has been developed, which affords exocyclic alkenyl tetrahydrocarbazoles in good chemical yields. This features convenient operation and tolerates a wide scope substrates variety electronically sterically diverse substituents. Furthermore, high E-stereoselectivity is observed for this reaction, provides an efficient method the preparation functionalized tetrahydrocarbazole derivatives.

Language: Английский

Citations

18

The synthesis of seven- and eight-membered rings by radical strategies DOI

Xuan-Chi Yu,

Cancan Zhang,

Ling‐Tao Wang

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(17), P. 4757 - 4781

Published: Jan. 1, 2022

Radical strategies for preparation of seven- or eight-membered rings.

Language: Английский

Citations

27

Electrochemical oxidative synthesis of 1,3,4-thiadiazoles from isothiocyanates and hydrazones DOI

Zhongxiao Ma,

Xiao Hu, Yanni Li

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(10), P. 2208 - 2214

Published: Jan. 1, 2021

A metal- and oxidant-free electrosynthesis of 2-amino-1,3,4-thiadiazoles through tandem addition/chemoselective C–S coupling.

Language: Английский

Citations

28

Heterogeneous visible-light promoted dehydrogenative [4 + 2] annulation of benzothioamides and alkynes under aerobic conditions DOI

Yanmin Guo,

Rong Chang,

Fu Zhen

et al.

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(13), P. 5206 - 5212

Published: Jan. 1, 2023

We have developed a visible-light induced dehydrogenative [4 + 2] annulation of benzothioamides and alkynes under aerobic conditions to synthesize isothiochromenes.

Language: Английский

Citations

12

Radical-polar Crossover Reaction of Glycine Derivatives DOI

Youwan Ye,

Xin Zhang,

Peng Kong

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(75), P. 10378 - 10381

Published: Jan. 1, 2024

Here we report a visible-light facilitated radical addition strategy for the preparation of various natural or unnatural α-amino acids from readily available glycine derivatives and alkenes. A key aspect in achieving this side carbon chain introduction reaction, while circumventing well-documented cyclization pathway, was employment radical-polar crossover under redox neutral conditions.

Language: Английский

Citations

5

Alkylation of Glycine Derivatives through a Synergistic Single-Electron Transfer and Halogen-Atom Transfer Process DOI

Peng Kong,

Youwan Ye,

Xin Zhang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7507 - 7513

Published: Aug. 29, 2024

Here, we present a versatile method for forming C(sp

Language: Английский

Citations

5

Solvent- and additive-free oxidative amidation of aldehydes using a recyclable oxoammonium salt DOI
Arturo León Sandoval, Katrina E. Doherty, Geoffrey P. Wadey

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(11), P. 2249 - 2254

Published: Jan. 1, 2022

A solvent- and additive-free oxidative functionalisation approach to prepare acyl azoles from aldehydes mediated by a substoichiometric quantity of recyclable oxoammonium salt.

Language: Английский

Citations

17

Chemodivergent Synthesis of Indeno[1,2-b]indoles and Isoindolo[2,1-a]indoles via Mn(III)-Mediated or Electrochemical Intramolecular Radical Cross-Dehydrogenative Coupling DOI

Piao Lu,

Weihui Zhuang,

Leipeng Lu

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(16), P. 10967 - 10981

Published: July 28, 2022

Chemodivergent synthesis of indeno[1,2-b]indoles and isoindolo[2,1-a]indoles from the same starting materials involving radical cross-dehydrogenative couplings have been developed. Mn(OAc)3·2H2O selectively promoted an intramolecular C–H/C–H dehydrogenative coupling reaction to provide indeno[1,2-b]indoles, while C–H/N–H could proceed via electrochemistry deliver isoindolo[2,1-a]indoles. Plausible mechanisms chemodivergent reactions were proposed.

Language: Английский

Citations

17