Silver- and Base-Enabled SOMOphilic Alkynylation of Alkylboronic Acids with Bromoalkynes DOI

Wenqian Du,

Rongjie Yang,

Jian-Shan Bai

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 8, 2025

Alkynyl-containing molecules hold significant importance in organic synthesis, drug discovery, and materials science. Herein, we report an efficient protocol for the C(sp)-C(sp3) cross-coupling of bromoalkynes with primary, secondary, tertiary alkylboronic acids. Mechanistic experiments suggest that silver base enable generation alkyl radical intermediate from acid then undergo a cascade α-addition β-elimination alkynyl bromides, leading to construction bonds. This strategy features readily available starting materials, diverse substrates, mild easily handled reaction conditions.

Language: Английский

Evaluation of mesoionic compound aromaticity using the HOMHED index DOI
Marcos A. P. Martins, Tainára Orlando, Jéssica M. L. Rosa

et al.

CrystEngComm, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Using HOMHED, mesoionic compounds were classified on an aromaticity continuum, demonstrating heteroatom influence and the balance between aromatic–betaine forms.

Language: Английский

Citations

0
Silver- and Base-Enabled SOMOphilic Alkynylation of Alkylboronic Acids with Bromoalkynes DOI

Wenqian Du,

Rongjie Yang,

Jian-Shan Bai

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 8, 2025

Alkynyl-containing molecules hold significant importance in organic synthesis, drug discovery, and materials science. Herein, we report an efficient protocol for the C(sp)-C(sp3) cross-coupling of bromoalkynes with primary, secondary, tertiary alkylboronic acids. Mechanistic experiments suggest that silver base enable generation alkyl radical intermediate from acid then undergo a cascade α-addition β-elimination alkynyl bromides, leading to construction bonds. This strategy features readily available starting materials, diverse substrates, mild easily handled reaction conditions.

Language: Английский

Citations

0