Aminoarylation of Alkynes using Diarylanilines DOI Creative Commons

Zi Liu,

Michael F. Greaney

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(49), P. 6296 - 6299

Published: Jan. 1, 2024

Intermolecular aminoarylation of alkynes is described,

Language: Английский

Energy-transfer-induced [3+2] cycloadditions of N–N pyridinium ylides DOI
Wooseok Lee, Yejin Koo, Hoimin Jung

et al.

Nature Chemistry, Journal Year: 2023, Volume and Issue: 15(8), P. 1091 - 1099

Published: June 26, 2023

Language: Английский

Citations

46
A general alkene aminoarylation enabled by N-centred radical reactivity of sulfinamides DOI
Efrey A. Noten, Cody Ng, Robert M. Wolesensky

et al.

Nature Chemistry, Journal Year: 2024, Volume and Issue: 16(4), P. 599 - 606

Published: Jan. 16, 2024

Language: Английский

Citations

35
Metal-free photocatalytic cross-electrophile coupling enables C1 homologation and alkylation of carboxylic acids with aldehydes DOI Creative Commons
Stefano Bonciolini, Antonio Pulcinella, Matteo Leone

et al.

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Feb. 19, 2024

In contemporary drug discovery, enhancing the sp

Language: Английский

Citations

19
Mechanism of Visible Light-Mediated Alkene Aminoarylation with Arylsulfonylacetamides DOI
Anthony R. Allen, Jia‐Fei Poon, Rory C. McAtee

et al.

ACS Catalysis, Journal Year: 2022, Volume and Issue: 12(14), P. 8511 - 8526

Published: July 1, 2022

Alkene aminoarylation with arylsulfonylacetamides via a visible-light mediated radical Smiles-Truce rearrangement represents convenient approach to the privileged arylethylamine pharmacaphore traditionally generated by circuitous, multi-step sequences. Herein, we report detailed synthetic, spectroscopic, kinetic, and computational studies designed interrogate proposed mechanism, including key aryl transfer event. The data are consistent rate-limiting 1,4-aryl migration occurring either stepwise process involving Meisenheimer-like intermediate or in concerted fashion dependent on both arene electronics alkene sterics. Our efforts probe mechanism have significantly expanded substrate scope of transformation respect migrating group provide further credence synthetic potential migrations.

Language: Английский

Citations

42
Photoinduced difunctionalization with bifunctional reagents containing N-heteroaryl moieties DOI
Wooseok Lee, Inyoung Park, Sungwoo Hong

et al.

Science China Chemistry, Journal Year: 2023, Volume and Issue: 66(6), P. 1688 - 1700

Published: May 10, 2023

Language: Английский

Citations

28
Photoredox catalytic alkylarylation of alkynes with arylsulfonylacetate as bifunctional reagent DOI

Chonglong He,

Min Wang, Yulong Wang

et al.

Science China Chemistry, Journal Year: 2024, Volume and Issue: 67(6), P. 2022 - 2028

Published: March 7, 2024

Language: Английский

Citations

9
Photocatalytic Alkylation of C(sp3)−H Bonds Using Sulfonylhydrazones** DOI Creative Commons
Antonio Pulcinella, Stefano Bonciolini, Florian Lukas

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 62(3)

Published: Nov. 17, 2022

The ability to construct C(sp3 )-C(sp3 ) bonds from easily accessible reagents is a crucial, yet challenging endeavor for synthetic organic chemists. Herein, we report the realization of such cross-coupling reaction, which combines N-sulfonyl hydrazones and )-H donors through diarylketone-enabled photocatalytic hydrogen atom transfer subsequent fragmentation obtained alkylated hydrazide. This mild metal-free protocol was employed prepare wide array alkyl-alkyl cross-coupled products tolerant variety functional groups. application this chemistry further provides preparatively useful route various medicinally-relevant compounds, as homobenzylic ethers, aryl ethyl amines, β-amino acids other moieties are commonly encountered in approved pharmaceuticals, agrochemicals natural products.

Language: Английский

Citations

32
A free-radical design featuring an intramolecular migration for a synthetically versatile alkyl–(hetero)arylation of simple olefins DOI Creative Commons

Dylan J. Babcock,

Andrew J. Wolfram,

Jaxon L. Barney

et al.

Chemical Science, Journal Year: 2024, Volume and Issue: 15(11), P. 4031 - 4040

Published: Jan. 1, 2024

A free-radical approach featuring an intramolecular aryl migration has significantly expanded the scope for alkyl–(hetero)arylation of simple olefins. It was also leveraged as key step in a new synthesis recently approved pharmaceutical.

Language: Английский

Citations

8
A radical Smiles rearrangement difunctionalization of activated alkenes via desulfonylation and insertion of sulfur dioxide relay strategy DOI

Si‐Wei Tian,

Zhentao Luo,

Biquan Xiong

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(11), P. 6774 - 6778

Published: Jan. 1, 2024

A novel and attractive photochemical difunctionalization of N -tosyl acrylamide for constructing alkylsulfonylated oxindoles amides with excellent substrate adaptability via a radical Smiles rearrangement strategy is described.

Language: Английский

Citations

7
Asymmetric, Remote C(sp3)−H Arylation via Sulfinyl‐Smiles Rearrangement DOI Creative Commons
Yawen Hu, Cédric Hervieu, Estı́baliz Merino

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(17)

Published: March 20, 2024

Abstract An efficient asymmetric remote arylation of C(sp 3 )−H bonds under photoredox conditions is described here. The reaction features the addition radicals to a double bond followed by site‐selective radical translocation (1, n ‐hydrogen atom transfer) as well stereocontrolled aryl migration via sulfinyl‐Smiles rearrangement furnishing wide range chiral α ‐arylated amides with up >99 : 1 er. Mechanistic studies indicate that sulfinamide group governs stereochemistry product being rate determining step preceded kinetically favored 1, ‐HAT process.

Language: Английский

Citations

6