Cathodic DeoxygenativeAlkylation of Nitro(hetero)areneswith Organic Halides

We have realized a cathodic deoxygenative alkylation between nitro(hetero)arenes and organic halides, employing bis(pinacolato)diboron (B<sub>2</sub>pin<sub>2</sub>) and LiCl as additives to trap and stabilize the generated alkyl radicals and carbanions, thereby facilitating efficient N–O cleavage and selective C–N bond formation. The protocol offers an economical method for the efficient synthesis of multiple aromatic(hetero) amines, without the need for reactive reductants and the exclusion of air and moisture. Notably, the protocol is distinguished by scalability, broad functional group compatibility, and safe and mild conditions, demonstrating practicality in the synthesis and late-stage modification of various bioactive compounds.

Publication Details

Journal
Figshare
Published
2025-01-28
DOI
https://doi.org/10.1021/acs.orglett.4c04792.s001
Primary Topic
Organoboron and organosilicon chemistry
Type
article
Field-Weighted Citation Impact
0.00
Controls
|||
ALL TIME
JAN
FEB
MAR
APR
MAY
JUN
JUL
AUG
SEP
OCT
article

Cathodic DeoxygenativeAlkylation of Nitro(hetero)areneswith Organic Halides

Figshare
Organoboron and organosilicon chemistry
article

Cathodic DeoxygenativeAlkylation of Nitro(hetero)areneswith Organic Halides

article en

Abstract

We have realized a cathodic deoxygenative alkylation between nitro(hetero)arenes and organic halides, employing bis(pinacolato)diboron (B<sub>2</sub>pin<sub>2</sub>) and LiCl as additives to trap and stabilize the generated alkyl radicals and carbanions, thereby facilitating efficient N–O cleavage and selective C–N bond formation. The protocol offers an economical method for the efficient synthesis of multiple aromatic(hetero) amines, without the need for reactive reductants and the exclusion of air and moisture. Notably, the protocol is distinguished by scalability, broad functional group compatibility, and safe and mild conditions, demonstrating practicality in the synthesis and late-stage modification of various bioactive compounds.

Figshare
Openalex Percentile: Top 63%
Organoboron and organosilicon chemistry
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.

Cathodic DeoxygenativeAlkylation of Nitro(hetero)areneswith Organic Halides · Figshare (2025) | TGRS Research Map | TGRS