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Probing Limits of a C=C Bond Activation by N-Coordinated Organopnictogen(I) Compounds
Authors: Kremláček Vít | Hejda Martin | Rychagova Elena | Ketkov Sergey | Jambor Roman | Růžička Aleš | Dostál Libor
Year: 2021
Type of publication: článek v odborném periodiku
Name of source: European Journal of Inorganic Chemistry
Publisher name: Wiley-VCH
Place: Weinheim
Page from-to: 4030-4041
Titles:
Language Name Abstract Keywords
cze Limity aktivace C=C vazby pomocí N-koordinovaných organopnictogenů(I) Byly zkoumány reakce N-koordinovaných organopnictogenů(I) s násobnými vazbami C=C. C=C vazby; N-koordinované organopnictogeny
eng Probing Limits of a C=C Bond Activation by N-Coordinated Organopnictogen(I) Compounds The C=C bond in selected N-alkyl/aryl-maleimides RN(C(O)CH)(2) (R=Me, tBu, Ph) is activated by organopnictogen(I) compounds producing bridged bicyclic [2.2.1] products exhibiting both endo and exo orientations. This is achieved by a synergic element-ligand cooperation, thereby resembling a hetero-Diels-Alder reaction. A wide range of pnictogen(I) complexes is considered in this study including the bis(aldiminine) pincer compounds ArE (1) (Ar=2,6-(R'N=CH)(2)C6H3, R'=tBu, E=P (P-1), As (As-1), Sb (Sb-1), Bi (Bi-1) or R'=Dmp, E=P (P-1'), As (As-1'), Sb (Sb-1'), where Dmp=2,6-Me2C6H3) and the C,N-coordinated compounds Ar'E (2) (Ar'=2-(DippN=CH)C6H4, E=P (P-2), As (As-2), where Dipp=2,6-iPr(2)C(6)H(3)). On this set of compounds, the reversibility of C=C bond activation was examined mainly by means of the H-1 variable temperature (VT) NMR spectroscopy and this study revealed trends showing a dependence both on the E atom and on the structure of the ligand. The structure of the addition products was elucidated by multinuclear NMR and single-crystal X-ray diffraction analysis. The whole study is accompanied by a theoretical survey targeting decisive factors for the C=C bond activation and a preference for endo/exo forms by the particular pnictogen(I) compound. C-C activation; Diels-Alder reaction; Heterocycles; Heterodienes; Pnictogens

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