Work

Regioselective formal hydrocyanation of allenes: synthesis of β,γ-unsaturated nitriles with α-all-carbon quaternary centers

Year: 2025

Type: article

Abstract: This study introduces a highly selective hydrocyanation method based on copper-catalyzed hydroalumination of allenes with diisobutylaluminum hydride, followed by the regio- and stereoselective allylation with p -toluenesulfonyl cyanide. The proposed methodology is efficient for accessing acyclic β,γ-unsaturated nitriles with α-all-carbon quaternary centers and achieves yields up to 99% and excellent regio- and E -selectivity. The reaction proceeds under mild conditions and shows broad applicability to di- and trisubstituted allenes. Its practicality is demonstrated through the gram-scale synthesis and functional group transformations of amines, amides, and lactams, emphasizing its versatility and synthetic significance.

Source: Beilstein Journal of Organic Chemistry

DOI: 10.3762/bjoc.21.63

Authors: Seeun Lim, Teresa Kim, Yunmi Lee

Institution: Kwangwoon University

Language: English

Topic: Catalytic Alkyne Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: National Research Foundation, National Research Foundation of Korea

Awards: G3745585056, G5532998691, G7856289270, G8501665801