Synthesis and Reactivity of a Crystalline Zinc–cAAC Radical

S Shuilian Xu (Key Laboratory of Organic Synthesis of Jiangsu Province & State Key Laboratory of Bioinspired Interfacial Materials Science, College of Chemistry, Chemical Engineering and Materials Science Soochow University Suzhou 215123 P.R. China) Y Yizhen Chen (Key Laboratory of Bioinorganic and Synthetic Chemistry of Ministry of Education, Guangdong Basic Research Center of Excellence for Functional Molecular Engineering, School of Chemistry, IGCME) S Shengjie Jiang (Key Laboratory of Organic Synthesis of Jiangsu Province & State Key Laboratory of Bioinspired Interfacial Materials Science, College of Chemistry, Chemical Engineering and Materials Science Soochow University Suzhou 215123 P.R. China) G Gengwen Tan (Key Laboratory of Bioinorganic and Synthetic Chemistry of Ministry of Education, Guangdong Basic Research Center of Excellence for Functional Molecular Engineering, School of Chemistry, IGCME) X Xin Xu

Abstract

AbstractReaction of LAmZnI [LAm = tBuC(N‐DIPP)2, DIPP = 2,6‐iPr2‐C6H3] with KC8 in the presence of cyclic (alkyl)(amino)carbene (cAAC) affords a stable radical complex [LAmZn(cAAC)]• (3). Single‐crystal structural analysis of 3 shows a short Zn─C bond and concomitant elongation of C─N bond within the cAAC ligand, indicating a significant π‐backbonding from the metal to the cAAC ligand. EPR spectroscopy and DFT calculations reveal that the spin density is mainly localized on the carbenic carbon atom, with a small portion on the zinc center. Complex 3 exhibits zinc‐centered radical reactivity as demonstrated by reactions with 2,2,6,6‐tetramethyl‐1‐piperidinyloxy, iodobenzene, trimethylsilyl azide, and [FeCp(CO)2]2, all of which occur at the zinc center and yield the corresponding Zn(II) complexes.

Article Details

Volume / Issue Vol. 64, Issue 43
Published October 20, 2025
ISSN 1433-7851
Publisher Wiley

Journal Info

Angewandte Chemie International Edition

Wiley

ISSN: 1433-7851 Physical Sciences

Authors (5)

S

Shuilian Xu

Key Laboratory of Organic Synthesis of Jiangsu Province & State Key Laboratory of Bioinspired Interfacial Materials Science, College of Chemistry, Chemical Engineering and Materials Science Soochow University Suzhou 215123 P.R. China

Y

Yizhen Chen

Key Laboratory of Bioinorganic and Synthetic Chemistry of Ministry of Education, Guangdong Basic Research Center of Excellence for Functional Molecular Engineering, School of Chemistry, IGCME

S

Shengjie Jiang

Key Laboratory of Organic Synthesis of Jiangsu Province & State Key Laboratory of Bioinspired Interfacial Materials Science, College of Chemistry, Chemical Engineering and Materials Science Soochow University Suzhou 215123 P.R. China

G

Gengwen Tan

Key Laboratory of Bioinorganic and Synthetic Chemistry of Ministry of Education, Guangdong Basic Research Center of Excellence for Functional Molecular Engineering, School of Chemistry, IGCME

X

Xin Xu