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Cyaphide-Azide 1,3-Dipolar Cycloaddition Reactions: Scope and Applicability.

ABSTRACT: Several examples of the cyaphide-azide 1,3-dipolar cycloaddition reaction to afford metallo-triazaphospholes are reported. The gold(I) triazaphospholes Au(IDipp)(CPN₃ R) (IDipp=1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene; R=^t Bu, Ad, Dipp), magnesium(II) triazaphospholes, {Mg(^Dipp NacNac)(CPN₃ R)}₂ (^Dipp NacNac=CH{C(CH₃ )N(Dipp)}₂ , Dipp=2,6-diisopropylphenyl; R=^t Bu, Bn), and germanium(II) triazaphosphole Ge(^Dipp NacNac)-(CPN₃ ^t Bu) can be prepared straightforwardly, under mild conditions and in good yields, in a manner reminiscent of the classic alkyne-azide click reaction (albeit without a catalyst). This reactivity can be extended to compounds with two azide functional groups such as 1,3-diazidobenzene. It is shown that the resulting metallo-triazaphospholes can be used as precursors to carbon-functionalized species, including protio- and iodo-triazaphospholes.

SUBMITTER: Yang ES

PROVIDER: S-EPMC10946888 | biostudies-literature | 2023 Sep

REPOSITORIES: biostudies-literature

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Cyaphide-Azide 1,3-Dipolar Cycloaddition Reactions: Scope and Applicability.

Yang Eric S ES Mapp Alex A Taylor Andrew A Beer Paul D PD Goicoechea Jose M JM

Chemistry (Weinheim an der Bergstrasse, Germany) 20230810 52

Several examples of the cyaphide-azide 1,3-dipolar cycloaddition reaction to afford metallo-triazaphospholes are reported. The gold(I) triazaphospholes Au(IDipp)(CPN3 R) (IDipp=1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene; R=t Bu, Ad, Dipp), magnesium(II) triazaphospholes, {Mg(Dipp NacNac)(CPN3 R)}2 (Dipp NacNac=CH{C(CH3 )N(Dipp)}2 , Dipp=2,6-diisopropylphenyl; R=t Bu, Bn), and germanium(II) tr ...[more]

PMID: 37338223

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