Late‐stage Functionalization using a Popular Titrating Agent: Aryl‐Chlorides and ‐Fluorides Activation by the Diphenylacetic Acid Dianion DOI Creative Commons

Alessandro Cerveri,

Giulia Russo, Sara Sparascio

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 31(8)

Published: Oct. 27, 2024

Abstract Aryl‐chlorides and ‐fluorides are common building blocks, but their use in synthesis is limited by the high stability of Ar−X bonds. The generation aryl radicals via activation strong bonds possible through irradiation tailor‐made organic anions, which become reductants stronger than lithium metal. We report that combination visible light with cheap diphenylacetic acid dianion an even better tool, showing excellent activity across a variety complex substrates providing opportunities for late‐stage drug modification. chemoselectively activated presence more easily reducible functions, such as Alk‐Cl ones carbonyl groups. These results pave way to original synthetic strategies would be otherwise considered impossible.

Language: Английский

Green synthesis for diverse bioactive benzo-fused spiroindolines through DBU-catalysed post-Ugi double cyclization DOI
Shuang Zhao, Mengxiao Chen,

Wenlu Zhou

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(41), P. 5455 - 5458

Published: Jan. 1, 2024

A metal-free protocol utilizing DBU catalysis for post-Ugi amide-ester exchange and Conia-ene double cyclization has been successfully developed, allowing the synthesis of diverse highly functionalized benzo-fused spiroindolines with anti-cancer activities under mild conditions.

Language: Английский

Citations

4
Synthesis of cis-fused cyclopentenone-pyrrolidine scaffolds via sequential aza-Piancatelli and Conia-ene type reactions in one pot DOI

Pooja R. Solanke,

Prakash Kumar, Prathama S. Mainkar

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(31), P. 4234 - 4237

Published: Jan. 1, 2024

A novel diastereoselective one-pot protocol has been developed through sequential execution of an aza-Piancatelli rearrangement and a Conia-ene type reaction under Lewis acid catalysis.

Language: Английский

Citations

3
Late-stage functionalization using a popular titrating agent: aryl- chlorides and -fluorides activation by the diphenylacetic acid dianion DOI Creative Commons

Alessandro Cerveri,

Giulia Russo, Sara Sparascio

et al.

Published: Aug. 8, 2024

Aryl-chlorides and -fluorides are common building blocks, but their use in synthesis is limited by the high stability of Ar-X bonds. The generation aryl radicals via activation strong bonds possible through irradiation tailor-made organic anions, which become reductants stronger than lithium metal. We report that combination visible light with cheap diphenylacetic acid dianion an even better tool, showing excellent activity across a variety complex substrates providing opportunities for late-stage drug modification. chemoselectively activated presence more easily reducible functions, such as Alk-Cl ones carbonyl groups, reminding Marcus inverted region principle. These results pave way to original synthetic strategies would be otherwise considered impossible

Language: Английский

Citations

1
Cs2CO3 Promoted [4 + 2] Cycloaddition of 1,6-Enynes: An Approach to Tetrahydro-1H-benzo-f-isoindole Isomers DOI
Xu Wang,

Junhao Yin,

Wangqin Mao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7757 - 7762

Published: Sept. 3, 2024

A Cs

Language: Английский

Citations

1
Late‐stage Functionalization using a Popular Titrating Agent: Aryl‐Chlorides and ‐Fluorides Activation by the Diphenylacetic Acid Dianion DOI Creative Commons

Alessandro Cerveri,

Giulia Russo, Sara Sparascio

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 31(8)

Published: Oct. 27, 2024

Abstract Aryl‐chlorides and ‐fluorides are common building blocks, but their use in synthesis is limited by the high stability of Ar−X bonds. The generation aryl radicals via activation strong bonds possible through irradiation tailor‐made organic anions, which become reductants stronger than lithium metal. We report that combination visible light with cheap diphenylacetic acid dianion an even better tool, showing excellent activity across a variety complex substrates providing opportunities for late‐stage drug modification. chemoselectively activated presence more easily reducible functions, such as Alk‐Cl ones carbonyl groups. These results pave way to original synthetic strategies would be otherwise considered impossible.

Language: Английский

Citations

0