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Updated: Jul 25, 2025

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Published on: May 26, 2019
Synthesis and Reactivity of a Zinc Diazoalkyl Complex: [3+2] Cycloaddition Reaction with Carbon Monoxide
Shengjie Jiang1, Yanping Cai1, Thayalan Rajeshkumar2
1Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, 215123, P. R. China.
Abstract:
This work reports the synthesis, characterization, and reactivity of the first example of a well-defined zinc α-diazoalkyl complex. Treatment of zinc(I)-zinc(I) bonded compound L2 Zn2 [L=CH3 C(2,6-i Pr2 C6 H3 N)CHC(CH3 )(NCH2 CH2 PPh2 )] or zinc(II) hydride LZnH with trimethylsilyldiazomethane affords zinc diazoalkyl complex LZnC(N2 )SiMe3 . This complex liberates N2 in the presence of a nickel catalyst to form an α-zincated phosphorus ylide by reacting with the pendant phosphine. It selectively undergoes formal [3+2] cycloaddition with CO2 or CO to form the corresponding product with a five-membered heterocyclic core. Notably, the use of CO in such a [3+2] cycloaddition reaction is unprecedented, reflecting a novel CO reaction mode.
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