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Tetraarylethylenes from Diarylmethanones and Hexachlorodisilane: The “Sila‐McMurry” Reaction
Author(s) -
Moxter Maximilian,
Tillmann Jan,
Füser Matthias,
Bolte Michael,
Lerner HansWolfram,
Wagner Matthias
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201603720
Subject(s) - aryl , chemistry , lewis acids and bases , coupling reaction , reaction conditions , medicinal chemistry , sequence (biology) , stereochemistry , organic chemistry , catalysis , biochemistry , alkyl
Hexachlorodisilane reacts with diarylmethanones (aryl=C 6 H 5 , 4‐MeC 6 H 4 , 4‐ t BuC 6 H 4 , 4‐ClC 6 H 4 , 4‐BrC 6 H 4 ) to furnish the corresponding tetraarylethylenes in good yields. The reductive conversion requires temperatures of about 160 °C and reaction times of 60–72 h. In the initial step, the Lewis‐basic carbonyl groups likely generate low‐valent [SiCl 2 ] as an analogue of [TiCl 2 ] in the classical McMurry reaction. The coupling sequence further proceeds via benzopinacolones, which have been isolated as key intermediates.