Synthesis and Reactivity of a Zinc Diazoalkyl Complex: [3+2] Cycloaddition Reaction with Carbon Monoxide.
Angew Chem Int Ed Engl
; 62(34): e202307244, 2023 Aug 21.
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| ID: mdl-37358377
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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MEDLINE
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En
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Angew Chem Int Ed Engl
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2023
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Article