Ligand-Controlled Preparation of Aryl-Substituted Allenes Enabled by Nickel-Catalyzed Reductive Coupling of Secondary Propargylic Carbonates with Aryl Halides

Herein, we developed a new method for the synthesis of aryl-substituted allenes through a nickel-catalyzed reductive coupling reaction between secondary propargyl carbonates and aryl halides. By employing the dimethyl-1,10-phenanthroline ligand, we achieved a ligand-controlled, regioselective nickel-catalyzed reductive arylation, overcoming the structural limitations of propargyl electrophiles. Notably, this reaction exhibits exceptional functional group compatibility, rendering it particularly suitable for late-stage allenylation modifications of complex molecules.

Authors

Institutions

Publication Details

Journal
Organic Letters
Published
2025-04-15
DOI
https://doi.org/10.1021/acs.orglett.5c01235
Citations
1
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.94

Funders

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

Ligand-Controlled Preparation of Aryl-Substituted Allenes Enabled by Nickel-Catalyzed Reductive Coupling of Secondary Propargylic Carbonates with Aryl Halides

Hegui Gong, Wenhai Huang, Jie Hu, Ruotong Li et al.
1 citations
Organic Letters
Catalytic C–H Functionalization Methods
0.94
article

Ligand-Controlled Preparation of Aryl-Substituted Allenes Enabled by Nickel-Catalyzed Reductive Coupling of Secondary Propargylic Carbonates with Aryl Halides

Hegui Gong, Wenhai Huang, Jie Hu, Ruotong Li, Yonghao Xi
article en
1 citations

Abstract

Herein, we developed a new method for the synthesis of aryl-substituted allenes through a nickel-catalyzed reductive coupling reaction between secondary propargyl carbonates and aryl halides. By employing the dimethyl-1,10-phenanthroline ligand, we achieved a ligand-controlled, regioselective nickel-catalyzed reductive arylation, overcoming the structural limitations of propargyl electrophiles. Notably, this reaction exhibits exceptional functional group compatibility, rendering it particularly suitable for late-stage allenylation modifications of complex molecules.

Organic LettersVol. 27(16)
Shanghai University (CN), Henan University (CN), Center for NanoScience (DE), College of Medical Sciences (NP)
Natural Science Foundation of Shanghai, National Natural Science Foundation of China
Openalex Percentile: Top 27%
Catalytic C–H Functionalization Methods
0.94
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.