Silylating Disulfides and Thiols with Hydrosilicones Catalyzed by B(C₆F₅)₃ Journal Articles

abstract

• AbstractHydrosilanes and silicones, catalyzed with B(C6F5)3, may be used to silylate thiols or cleave disulfides giving silyl thio ethers. Alcohols were found to react faster than thiols or disulfides, while alkoxysilanes (the Piers‐Rubinsztajn reaction) were slower such that the overall order of reactivity was found to be HO>HS>SS>SiOEt. The resulting silane and silicone‐protected thio ethers produced from the sulfur‐based functional groups could be cleaved to thiols using alcohols or mild acid with rates that depend on the steric bulk of the siloxane.

authors

• Liao, Mengchen
• Zheng, Sijia
• Brook, Michael Adrian

status

• published 

publication date

• May 14, 2021

has subject area

• 0304 Medicinal and Biomolecular Chemistry (FoR)
• 0305 Organic Chemistry (FoR)
• Organic Chemistry (Science Metrix)

published in

• European Journal of Organic Chemistry  Journal

keywords

• BORANE
• CHEMISTRY
• Chemistry
• Chemistry, Organic
• Coupling agent
• Hydrosiloxane
• Physical Sciences
• Piers-Rubinsztajn
• SI-H
• Science & Technology
• Thiol
• Thiol protection
• disulfide reduction

Digital Object Identifier (DOI)

• 10.1002/ejoc.202100349

start page

• 2694

end page

• 2700

volume

• 2021

issue

• 18