Iron-catalyzed azidation of cyclobutanol by C C bond cleavage DOI
Xiaoyuan Liu, Limei Wang,

Jincheng Zhan

et al.

Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 140, P. 155016 - 155016

Published: March 19, 2024

Language: Английский

Strained cycloalkanols in C–C bond formation reactions: a boon in disguise! DOI
Neha Jha, P. Mishra, Manmohan Kapur

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(19), P. 4941 - 4971

Published: Jan. 1, 2023

A summary of the various ring opening reactions strained and unstrained cycloalkanols is elaborated in present review. Key emphasis on reactivities pertaining to cyclopropanols, cyclobutanols higher analogues provided.

Language: Английский

Citations

14
Unlock the C–N Bond Amidation of Enaminones: Metal-Free Synthesis of Enamides by Water-Assisted Transamidation DOI

Haozhi Wu,

Kang Chen, Yunyun Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(1), P. 216 - 223

Published: Dec. 18, 2023

The C–N bond transamidation of primary amides with N,N-dimethyl enaminones has been efficiently realized by heating in the presence trifluoromethanesulfonic acid (TfOH). method enables practical synthesis valuable enamides without use any metal reagent. In addition, this protocol can also be expanded to reactions sulfonamides, and late-stage functionalization on sulfonamide drugs such as Celecoxib Valdecoxib verified. Moreover, participation water assisting process identified isotope labeling experiments using D2O, disclosing a new possibility designing catalytic tactic other reactions.

Language: Английский

Citations

14
Rhodium(III)-Catalyzed Switchable β-C(sp2)–H Alkenylation and Alkylation of Acyclic Enamides with Allyl Alcohols DOI
Xiaolan Li, Jie Liu,

Ruixin Song

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(17), P. 3673 - 3678

Published: April 19, 2024

Herein, rhodium(III)-catalyzed β-C(sp2)–H alkenylation and alkylation of enamides are presented using readily accessible allylic alcohols by switching the reaction conditions. This tunable transformation has been applied to a wide range substrates typically proceeded with excellent regioselectivity stereoselectivity as well good functional group tolerance. The catalytic system offers an efficient approach for synthesizing various functionalized bearing N-(2Z,4E)-butadiene (Z)-β-C(sp2)–H alkylated enamides. In addition, mechanistic experiments suggest that Rh(III)-catalyzed C–H activation is not related critical step.

Language: Английский

Citations

6
Photocatalytic C(sp2)–H sulfamoylation of enamides: regio- and stereoselective construction of (E)-β-sulfamoyl enamides DOI

Ling-Li Liu,

Yechun Wu,

Xian Wu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(21), P. 5470 - 5477

Published: Jan. 1, 2023

A photocatalytic, regio- and stereoselective olefinic β-C–H sulfamoylation of enamides with commercially available sulfamoyl chlorides was developed.

Language: Английский

Citations

12
Visible-light-induced tandem ring opening/1,6-conjugate addition of cyclobutanols with p-quinone methides under metal- and additive-free conditions DOI

Tongyao Zhou,

Jie Zeng, Yang Liu

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(3), P. 1375 - 1380

Published: Jan. 1, 2024

A visible-light-mediated tandem ring opening/1,6-conjugate addition of cyclobutanols with p -quinone methides was developed. This protocol allowed the formation δ,δ-diaryl ketones in presence a readily available organic photocatalyst.

Language: Английский

Citations

5
Photocatalytic chemo-, regio- & stereoselective olefinic β-C–H decarboxylative alkylation of enamides with diacyl peroxides DOI

Han Liu,

Yechun Wu,

Lingli Liu

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(55), P. 8556 - 8559

Published: Jan. 1, 2023

A decarboxylative alkylation of enamides with alkyl diacyl peroxides induced by visible-light is described. The chemo-, regio- and stereoselective olefinic β-C-H generates a series primary- secondary alkylated in yields up to 95%. This transformation bears the advantages operational simplicity, good functional group compatibility mild conditions.

Language: Английский

Citations

9
Direct β-C–H ketoalkylation of enaminoesters with cyclopropanols under metal-free conditions DOI
Jun‐Long Zhan,

Sai-Nan Zhou,

Yu Wang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A TEMPO-mediated β-ketoalkylation of enaminoesters with cyclopropanols under metal-free conditions is herein described. This reaction provides a straightforward and highly efficient route to β-keto alkyl substituted for the first time, which could be rapidly efficiently converted into synthetically useful 2-alkoxycarbonyl functionalized 1,5-diketones. Moreover, practicability this protocol successfully demonstrated by scale-up experiments late-stage functionalization natural products pharmaceutically relevant molecules.

Language: Английский

Citations

0
Rhodium(III)-catalyzed selective C−H olefination and desilylative vinylation of acyclic enamides with vinylsilanes DOI
Xiaolan Li, Jie Liu,

Ruixin Song

et al.

Journal of Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 116051 - 116051

Published: March 1, 2025

Language: Английский

Citations

0
Photocatalytic Three-Component Radical Sulfonarylation of Alkenes: Preparation of γ-Keto-Sulfone-Substituted Oxindoles DOI
Fei Chen,

Jun-Ya Guo,

Yunhong Jia

et al.

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

Published: March 16, 2025

A photocatalytic radical sulfonarylation of N-arylacrylamides via a three-component cascade cyclopropyl alcohol ring opening/sulfur dioxide insertion/sulfonyl addition/cyclization sequence has been developed. This method employs alcohols as the precursors β-carbonyl alkyl radicals and Na2S2O5 cheap source sulfur dioxide. By using this procedure, wide variety γ-keto-sulfone-substituted oxindoles were facilely synthesized.

Language: Английский

Citations

0
Strategic Synthesis of γ-Nitroketones between Nitroalkanes and Cyclopropanols: Harnessing Free-Radical Nucleophilic Substitution for Chemical Innovation DOI

Yi-Wei Xu,

Zhongyu Zhang,

Cong Wei

et al.

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

Published: March 25, 2025

The alkylation of nitro compounds is an efficient technique to augment molecular complexity, as exemplified by the Henry reaction and Michael addition involving sp2-hybridized carbon. However, a challenge arises in with sp3-hybridized carbon due competing nonproductive O-alkylation. In this study, we have developed manganese-promoted oxidative nitroalkanes using cyclopropyl alcohols via solvent-caged free-radical nucleophilic substitution pathway. This process yields variety γ-nitroketones, including sterically hindered tertiary nitroalkanes, thereby introducing novel approach for C-alkylation nitroalkanes. Subsequent reduction facilitates synthesis pyrroline pyrrolidine derivatives.

Language: Английский

Citations

0