[3+2] Cycloadditions of Aldiminoboranes with N -Acylpyrazoles

Abstract The [3+2] cycloaddition between aldiminoboranes and N-acylpyrazoles was successfully achieved. Aldiminoboranes, serving as C═N═B building blocks, were generated in situ via direct hydroboration of nitriles with Piers’ borane HB(C6F5)2. The [3+2] cycloaddition furnishes five-membered BN-heterocyclic compounds and notably features an acyl migration. Furthermore, the reaction exhibits a broad substrate scope with respect to both nitriles and N-acylpyrazoles, affording the target products in 56–87% isolated yields.

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Publication Details

Journal
Organic Letters
Published
2026-10-15
DOI
https://doi.org/10.1021/acs.orglett.6c04005
Primary Topic
Organoboron and organosilicon chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

[3+2] Cycloadditions of Aldiminoboranes with N -Acylpyrazoles

Tongdao Wang, Min Liu
Organic Letters
Organoboron and organosilicon chemistry
article

[3+2] Cycloadditions of Aldiminoboranes with N -Acylpyrazoles

Tongdao Wang, Min Liu
article en

Abstract

Abstract The [3+2] cycloaddition between aldiminoboranes and N-acylpyrazoles was successfully achieved. Aldiminoboranes, serving as C═N═B building blocks, were generated in situ via direct hydroboration of nitriles with Piers’ borane HB(C6F5)2. The [3+2] cycloaddition furnishes five-membered BN-heterocyclic compounds and notably features an acyl migration. Furthermore, the reaction exhibits a broad substrate scope with respect to both nitriles and N-acylpyrazoles, affording the target products in 56–87% isolated yields.

Organic Letters
Dalian University of Technology (CN), Dalian University (CN)
National Natural Science Foundation of China, Liaoning Revitalization Talents Program
Openalex Percentile: Top 25%
Organoboron and organosilicon chemistry
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