Gold-Catalyzed Intermolecular Assembly of Donor and Acceptor Fragments for [1,5]-Hydride Migrations

The [1,n]-hydride migration reactions represent one of the most powerful techniques to functionalize C(sp<sup>3</sup>)-H bonds and to rapidly construct molecular complexities. However, their substrates usually required multiple steps to prepare in advance. Herein, we developed a gold-catalyzed intermolecular coupling of hydride-donor-containing nucleophiles (amines) and hydride-acceptor-containing alkynes (1,3-diynamides) for cascade [1,5]-hydride migrations. Control experiments revealed the role of the dichloroethane solvent and the unexpected involvement of protonated anilines in promoting [1,5]-hydride migrations.

Authors

Institutions

Publication Details

Journal
Organic Letters
Published
2025-03-20
DOI
https://doi.org/10.1021/acs.orglett.5c00816
Primary Topic
Catalytic Alkyne Reactions
Type
article
Field-Weighted Citation Impact
0.00

Funders

Controls
|||
ALL TIME
JAN
FEB
MAR
APR
MAY
JUN
JUL
AUG
SEP
OCT
article

Gold-Catalyzed Intermolecular Assembly of Donor and Acceptor Fragments for [1,5]-Hydride Migrations

Youliang Wang, Yongliang Zhang, Xiaoqian Zhang, Ningbo Li
Organic Letters
Catalytic Alkyne Reactions
article

Gold-Catalyzed Intermolecular Assembly of Donor and Acceptor Fragments for [1,5]-Hydride Migrations

Youliang Wang, Yongliang Zhang, Xiaoqian Zhang, Ningbo Li
article en

Abstract

The [1,n]-hydride migration reactions represent one of the most powerful techniques to functionalize C(sp<sup>3</sup>)-H bonds and to rapidly construct molecular complexities. However, their substrates usually required multiple steps to prepare in advance. Herein, we developed a gold-catalyzed intermolecular coupling of hydride-donor-containing nucleophiles (amines) and hydride-acceptor-containing alkynes (1,3-diynamides) for cascade [1,5]-hydride migrations. Control experiments revealed the role of the dichloroethane solvent and the unexpected involvement of protonated anilines in promoting [1,5]-hydride migrations.

Organic LettersVol. 27(13)
Peking University (CN), Beijing National Laboratory for Molecular Sciences (CN), Xi'an Jiaotong University (CN)
National Natural Science Foundation of China, Fundamental Research Funds for the Central Universities
Reduced inequalities
Openalex Percentile: Top 96%
Catalytic Alkyne Reactions
AI Navigator

Ask Laika to Summarize, Analyze, and Connect papers live on the map.

Summarize Papers & Methodologies

Extract key findings, datasets, and comparative methods across publications.

Benchmark Rankings & Visual Analytics

Rank top research institutions, authors, funders, topics, and journals by Field-Weighted Citation Impact (FWCI) and paper volume with instant charts.

Connect Distant Disciplines

Bridge topological clusters on the map to find hidden collaborative intersections.