Site-Selective Gold-Catalyzed Alkylation of α-Aminotropones with Allenes DOI

Giulio Gallorini,

Sofia Kiriakidi,

Sara Bellini

et al.

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

Published: Oct. 21, 2024

The site-selective alkylation of α-aminotropones is effectively realized via gold(I)-catalyzed electrophilic activation allenamides and allenyl ethers, yielding up to 85% in 30 examples. A dedicated combined spectroscopic computational investigation accounts for both chemo- regioselective profiles the protocol. New opportunities chemical space tropone/tropolone derivatives are identified.

Language: Английский

Electrochemical Nickel-Catalyzed C(sp2)-H Functionalization of Tropones with Aldehydes DOI Creative Commons
Andrea Brunetti, Sofia Kiriakidi,

Mauro Garbini

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 3184 - 3190

Published: Feb. 6, 2025

A direct electroreductive functionalization of tropones employing aldehydes as alkylating agents is reported. This C(sp2)-H process leverages the mediation electroactive nickel complexes, enabling a wide range both native and substituted (44 examples) to be alkylated selectively at α-position in high yields (up 90%). Combined electrochemical, spectroelectrochemical, computational analyses disclosed whole mechanistic pathway revealed key role played by reduced Ni complexes activating tropone core toward condensation with aldehydes.

Language: Английский

Citations

1
Visible-light-mediated site-selective C(sp2)–H alkylation of tropones facilitates semi-synthesis of cephafortunoids A and B DOI Creative Commons
Q. Zeng, Cheng‐Yu Zheng,

Zhan‐Peng Ge

et al.

Chemical Science, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

An efficient visible-light-driven method for achieving α-site-selective C–H alkylation of tropones was developed. It applied to transform fortunolide A into cephafortunoids and B, marking the first synthesis C 20 Cephalotaxus troponoids.

Language: Английский

Citations

0
Electrochemical Synthesis of Itaconic Acid Derivatives via Chemodivergent Single and Double Carboxylation of Allenes with CO2 DOI
Andrea Brunetti,

Mauro Garbini,

Giuseppe Autuori

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(49)

Published: June 24, 2024

Abstract Leveraging electrochemistry, a new synthesis of non‐natural derivatives itaconic acid is proposed by utilizing carbon dioxide (CO 2 ) as valuable C1 synthon. An electrochemical cross‐electrophile coupling between allenoates and CO was targeted, allowing for the both mono‐ di‐carboxylation products in catalyst‐ additive‐free environment (yields up to 87 %, 30 examples). Elaboration model mono‐carboxylation product, detailed cyclovoltammetric, well mechanistic analyses complete present investigation.

Language: Английский

Citations

2
Site-Selective Gold-Catalyzed Alkylation of α-Aminotropones with Allenes DOI

Giulio Gallorini,

Sofia Kiriakidi,

Sara Bellini

et al.

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

Published: Oct. 21, 2024

The site-selective alkylation of α-aminotropones is effectively realized via gold(I)-catalyzed electrophilic activation allenamides and allenyl ethers, yielding up to 85% in 30 examples. A dedicated combined spectroscopic computational investigation accounts for both chemo- regioselective profiles the protocol. New opportunities chemical space tropone/tropolone derivatives are identified.

Language: Английский

Citations

2