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Expedient Synthesis of Thioether‐Functionalized Hydrotris(indazolyl)borate as an Anchoring Platform for Rotary Molecular Machines
Author(s) -
Erbland Guillaume,
Gisbert Yohan,
Rapenne Gwénaël,
Kammerer Claire
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800990
Subject(s) - thioether , chemistry , ruthenium , yield (engineering) , ligand (biochemistry) , boron , combinatorial chemistry , cyclopentadienyl complex , polymer chemistry , organic chemistry , catalysis , materials science , biochemistry , receptor , metallurgy
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 fivefold Suzuki–Miyaura coupling with ferroceneboronic acid led to a new C 5 ‐symmetric pentaferrocenyl molecular motor.