Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 7, Pages 2469-2475Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202004281
Keywords
conformational isomerism; coordination chemistry; electron density distribution; gold catalysis; phosphaalkenes
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Funding
- Ministry of Education, Culture, Sports, Science and Technology [19H02685]
- Nissan Chemicals Co. Ltd.
- Grants-in-Aid for Scientific Research [19H02685] Funding Source: KAKEN
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This study investigated the complexation of phosphanoxy-substituted phosphaalkenes with gold and evaluated their catalytic activity. It was found that a pseudo coordinating interaction exists between the gold center and the P=C unit, and the bis(chlorogold) complexes can catalyze various reactions without activation treatment.
The phosphanoxy-substituted phosphaalkene bearing the P=C-O-P skeleton can be prepared from diphosphene Mes*P=PMes* (Mes*=2,4,6-tBu(3)C(6)H(2)), and their use for catalysis is of interest. In this paper, complexation of the phosphanoxy-substituted phosphaalkenes with gold are investigated, and the catalytic activity of the mono- and bis(chlorogold) complexes are subsequently evaluated. Reaction of the P=C-O-P compound with (tht)AuCl (tht=tetrahydrothiophene) showed dominant coordination on the sp(3) phosphorus, and complete coordination on the sp(2) phosphorus required removal of tetrahydrothiophene. Atoms In Molecules (AIM) analysis based on the X-ray structure of the mono(chlorogold) complex indicated a pseudo coordinating interaction between the gold center and the P=C unit. The bis(chlorogold) complexes displayed conformational isomerism, and catalyzed the cycloisomerization/alkoxycyclization of 1,6-enyne and for hydration of terminal alkyne without activation treatment. Even the mono(chlorogold) complexes catalyzed the alkoxycyclization reactions without a silver co-catalyst, indicating that the alcohols were effective in activating the AuCl unit.
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