Synthesis of Functionalized Aliphatic Acid Esters via the Generation of Alkyl Radicals from Silylperoxyacetals DOI
Akira Matsumoto,

Yoko Shiozaki,

Shunya Sakurai

et al.

Chemistry - An Asian Journal, Journal Year: 2021, Volume and Issue: 16(17), P. 2431 - 2434

Published: July 19, 2021

Abstract We describe a catalytic method for the synthesis of variety functionalized aliphatic acid esters using silylperoxyacetals, which are versatile alkyl radical precursors with terminal ester moiety. In presence an appropriate transition‐metal catalyst, in situ generation radicals and subsequent bond‐forming process proceeds smoothly to afford synthetically valuable derivatives. The present can be applied efficient pharmaceutically important 1,1‐diarylalkane motif. addition, novel strategy structurally diverse hydroxy derivatives via C−O bond formation that utilizes TEMPO has been developed.

Language: Английский

Suzuki–Miyaura cross coupling reaction: recent advancements in catalysis and organic synthesis DOI
Brijesh S. Kadu

Catalysis Science & Technology, Journal Year: 2021, Volume and Issue: 11(4), P. 1186 - 1221

Published: Jan. 1, 2021

Suzuki–Miyaura cross coupling reaction (SMCR) – A milestone in the synthesis of C–C coupled compounds.

Language: Английский

Citations

145

Three-component 1,2-dicarbofunctionalization of alkenes involving alkyl radicals DOI
Pin Gao,

Yue-Jie Niu,

Fan Yang

et al.

Chemical Communications, Journal Year: 2021, Volume and Issue: 58(6), P. 730 - 746

Published: Dec. 8, 2021

This article provides a comprehensive perspective on three-component 1,2-dicarbofunctionalization of alkenes involving alkyl radicals, which generated from structurally diverse electrophilic and nucleophilic precursors under mild conditions.

Language: Английский

Citations

80

A cheap metal catalyzed ring expansion/cross-coupling cascade: a new route to functionalized medium-sized and macrolactones DOI Creative Commons
Shuai Liu, Pengchen Ma, Lu Zhang

et al.

Chemical Science, Journal Year: 2023, Volume and Issue: 14(19), P. 5220 - 5225

Published: Jan. 1, 2023

An efficient alkoxyl radical-triggered ring expansion/cross-coupling cascade was developed under cheap metal catalysis. Through the metal-catalyzed radical relay strategy, a wide range of medium-sized lactones (9-11 membered) and macrolactones (12, 13, 15, 18, 19-membered) were constructed in moderate to good yields, along with diverse functional groups including CN, N3, SCN, X installed concurrently. Density theory (DFT) calculations revealed that reductive elimination cycloalkyl-Cu(iii) species is more favorable reaction pathway for cross-coupling step. Based on results experiments DFT, Cu(i)/Cu(ii)/Cu(iii) catalytic cycle proposed this tandem reaction.

Language: Английский

Citations

18

Nickel‐Catalyzed Regioselective Intermolecular Dialkylation of Alkenylarenes: Generation of Two Vicinal C(sp3)−C(sp3) Bonds Across Alkenes** DOI Creative Commons

Daniel M. Lux,

Vivek Aryal,

Doleshwar Niroula

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(32)

Published: June 15, 2023

We disclose a Ni-catalyzed regioselective dialkylation reaction of alkenylarenes with α-halocarbonyls and alkylzinc reagents. The produces γ-arylated alkanecarbonyl compounds the generation two new C(sp

Language: Английский

Citations

16

Fe-Catalyzed Alkylazidation of α-Trifluoromethylalkenes: An Access to Quaternary Stereocenters Containing CF3 and N3 Groups DOI
Shuai Liu, Lu Zhang, Liang Xu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(8), P. 1336 - 1341

Published: Feb. 23, 2023

A concise Fe-catalyzed alkylazidation of α-trifluoromethylalkenes via a C–C bond cleavage/radical addition/azidation cascade is described. This protocol features broad substrate scope, excellent functional group compatibility, and the ability to be performed on gram scale, thus offering practical step-economic approach synthetically useful tertiary α-trifluoromethyl azides.

Language: Английский

Citations

14

Metal-free, visible-light driven C–H ketoalkylation of glycine derivatives and peptides DOI
Xin Hong,

Zi-Hang Yuan,

Mingyu Yang

et al.

Green Chemistry, Journal Year: 2021, Volume and Issue: 23(23), P. 9549 - 9553

Published: Jan. 1, 2021

A metal free, visible-light driven C–H ketoalkylation of glycine derivatives and peptides with cycloalkyl hydroperoxides is presented. This protocol provides diverse unnatural amino acids bearing a distal carbonyl group in moderate to good yields.

Language: Английский

Citations

32

Alkoxyl Radical-Mediated Ring Expansion/1,4-Difunctionalization of 1,3-Enynes upon Copper Catalysis DOI

Hong-Jie Miao,

Jinhua Zhang, Shuai Liu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(30), P. 5563 - 5568

Published: July 21, 2023

A redox-neutral copper-catalyzed cascade reaction involving alkoxyl radical-mediated ring expansion/1,4-difunctionalization of 1,3-enynes was developed, offering a straightforward approach to the tetra-substituted allenes with macrolactone, CN, and CF3 functional groups. Remarkably, incorporation NH2 group onto 1,3-enyne moiety enabled further cyclization give unique scaffold containing lactone an indole moiety.

Language: Английский

Citations

13

Three-Component Ru-Catalyzed Regioselective Alkylarylation of Vinylarenes via Meta-Selective C(sp2)–H Bond Functionalization DOI
Hongchao Liu,

Xiao-Ping Gong,

Yu‐Zhao Wang

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(16), P. 3043 - 3047

Published: April 18, 2022

We report a novel Ru-catalyzed regioselective alkylarylation of vinylarenes with alkyl halides and arenes via meta-C(sp2)-H bond functionalization to construct 1,1-diarylalkanes that generally show bioactivity. In this transformation, wide spectrum primary, secondary, tertiary electronically varied was well-tolerated. This reaction is characterized by its exquisite regioselectivity vinylarenes, unique selectivity, redox-neutral conditions. The mechanism presented supported radical probes kinetic isotope effect studies.

Language: Английский

Citations

19

Copper-Catalyzed 1,4-Alkylarylation of 1,3-Enynes with Ethers and Aryl Boronic Acids Enabled via C(sp3)–H Functionalization DOI
Yunhe Lv,

Weiya Pu,

Le Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(4), P. 1478 - 1488

Published: Jan. 17, 2025

Herein, we present a copper-catalyzed, three-component intermolecular 1,4-alkylarylation of 1,3-enynes with ethers and aryl boronic acids. This method, driven by α-C(sp3)-H functionalization the oxygen atom in ethers, regioselectively produces various tetrasubstituted allenes from simple, readily available precursors. Key features include mild reaction conditions simple catalytic system.

Language: Английский

Citations

0

Iron-Catalyzed Alkoxyl Radical-Induced C–C Bond Cleavage/gem-Difluoroalkylation Cascade DOI
Tianyu Zhang, Yong Wu, Shuai Liu

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(23), P. 4329 - 4334

Published: June 1, 2023

An inexpensive iron-catalyzed alkoxyl radical-induced C–C bond cleavage/gem-difluoroalkylation cascade is presented. Regulated by the structure of radical precursors, fluorinated distal diketones were synthesized through a ring-opening strategy and difluoroalkylated medium-sized lactones macrolactones constructed via ring-expansion strategy. Both protocols proceeded under mild redox neutral conditions with broad substrate scope good functional group compatibility.

Language: Английский

Citations

9