Expedient Synthesis of Thioether-Functionalized Hydrotris(indazolyl)borate as an Anchoring Platform for Rotary Molecular Machines - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2018

Expedient Synthesis of Thioether-Functionalized Hydrotris(indazolyl)borate as an Anchoring Platform for Rotary Molecular Machines

Résumé

Major improvements in the synthesis of surface-mounted rotary molecular machines based on ruthenium(II) complexes are reported. The development of a one-pot indium(III)-mediated "N-deprotection / ester reductive sulfidation" sequence allowed step economy, reproducibility and high efficiency in the synthesis of the thioether-functionalized tripodal ligand. Switching to the thallium salt of hydrotris(indazolyl)borate and to microwave heating further optimized the preparation of the common intermediate in the modular synthesis of symmetric and dissymmetric molecular motors and gears. The penta(4-bromophenyl)cyclopentadienyl ruthenium(II) key precursor is now reproducibly synthesized in 5 steps and 31% overall yield on the longest linear sequence. Subsequent five-fold Suzuki-Miyaura coupling with ferroceneboronic acid led to a new C5-symmetric penta-ferrocenyl molecular motor.

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Chimie
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Dates et versions

hal-01880748 , version 1 (12-05-2020)

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Guillaume Erbland, Yohan Gisbert, Gwénaël Rapenne, Claire Kammerer. Expedient Synthesis of Thioether-Functionalized Hydrotris(indazolyl)borate as an Anchoring Platform for Rotary Molecular Machines. European Journal of Organic Chemistry, 2018, 2018, pp.4731 - 4739. ⟨10.1002/ejoc.201800990⟩. ⟨hal-01880748⟩
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