Palladium-Catalyzed N-Allylic Alkylation of Pyrazoles and Unactivated Vinylcyclopropanes DOI

Shao-Jie Cheng,

Xin-Li Zhang,

Zhongyue Yang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 20, 2024

An efficient palladium-catalyzed N-allylic alkylation of pyrazoles and unactivated vinylcyclopropanes is demonstrated, affording various N-alkyl in ≤99% yield. This protocol displays high atom economy, a broad range substrates, excellent regioselectivity stereoselectivity. Late-stage modification bioactive molecules, scaled-up reaction, divergent derivatization documented the practicability this methodology. The preliminary mechanistic investigation hinted that Pd–H species promotes ring opening cyclopropanes.

Language: Английский

Rhodium-Catalyzed Asymmetric N2-C5 Allylation of Indazoles with Dienyl Allylic Alcohols DOI

Zhangru Cheng,

Peng Zhang,

Ying Shao

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(27), P. 5646 - 5651

Published: July 2, 2024

The development of site-selective and regio- enantioselective reactions substrates with multiple active sites is an important topic remains a substantial challenge in synthetic chemistry. Here, we describe rhodium-catalyzed asymmetric

Language: Английский

Citations

3
Chemo- and diastereoselective four-component reactions with Rh carbynoids DOI Creative Commons
Mengchu Zhang, Xiaoyan Yang, Xiang Fu

et al.

Green Synthesis and Catalysis, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 1, 2024

Language: Английский

Citations

2
Rhodium-Catalyzed Enantioselective Ring-Openings of Oxabicyclic Alkenes with Azole Nucleophiles DOI
Matthew T. Zambri,

Armaan Grewal,

Mark Lautens

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16889 - 16898

Published: Nov. 6, 2024

We report enantioselective ring-openings of oxabicyclic alkenes with azole nucleophiles, generating heterocycle-bearing dihydronaphthalene products. Pyrazoles, triazoles, tetrazoles, and benzo-fused derivatives participate in the ring-opening, level regioselectivity depending on type substitution pattern heterocyclic partner. Electron-withdrawing substituents have a beneficial effect, suppressing unproductive complexation nitrogen Rh(I)-bis(phosphine) catalyst.

Language: Английский

Citations

1
Palladium-Catalyzed N-Allylic Alkylation of Pyrazoles and Unactivated Vinylcyclopropanes DOI

Shao-Jie Cheng,

Xin-Li Zhang,

Zhongyue Yang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 20, 2024

An efficient palladium-catalyzed N-allylic alkylation of pyrazoles and unactivated vinylcyclopropanes is demonstrated, affording various N-alkyl in ≤99% yield. This protocol displays high atom economy, a broad range substrates, excellent regioselectivity stereoselectivity. Late-stage modification bioactive molecules, scaled-up reaction, divergent derivatization documented the practicability this methodology. The preliminary mechanistic investigation hinted that Pd–H species promotes ring opening cyclopropanes.

Language: Английский

Citations

0