Literature DB >> 27690327

Tetraarylethylenes from Diarylmethanones and Hexachlorodisilane: The "Sila-McMurry" Reaction.

Maximilian Moxter1, Jan Tillmann1, Matthias Füser1, Michael Bolte1, Hans-Wolfram Lerner1, Matthias Wagner2.   

Abstract

Hexachlorodisilane reacts with diarylmethanones (aryl=C6 H5 , 4-MeC6 H4 , 4-tBuC6 H4 , 4-ClC6 H4 , 4-BrC6 H4 ) 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 [SiCl2 ] as an analogue of [TiCl2 ] in the classical McMurry reaction. The coupling sequence further proceeds via benzopinacolones, which have been isolated as key intermediates.
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−C coupling; Sila-McMurry reaction; alkenes; dichlorosilylene; reaction mechanism

Year:  2016        PMID: 27690327     DOI: 10.1002/chem.201603720

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  1 in total

Review 1.  Recent advances of carbonyl olefination via McMurry coupling reaction.

Authors:  Anthony Bongso; Robby Roswanda; Yana Maolana Syah
Journal:  RSC Adv       Date:  2022-05-26       Impact factor: 4.036

  1 in total

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