463-30-9Relevant articles and documents
Covalently attached monolayers on crystalline hydrogen-terminated silicon: Extremely mild attachment by visible light
Sun, Qiao-Yu,De Smet, Louis C. P. M.,Van Lagen, Barend,Giesbers, Marcel,Thuene, Peter C.,Van Engelenburg, Johan,De Wolf, Frits A.,Zuilhof, Han,Sudhoelter, Ernst J. R.
, p. 2514 - 2523 (2005)
A very mild method was developed for the attachment of high-quality organic monolayers on crystalline silicon surfaces. By using visible light sources, from 447 to 658 nm, a variety of 1-alkenes and 1-alkynes were attached to hydrogen-terminated Si(IOO) and Si(111) surfaces at room temperature. The presence and the quality of the monolayers were evaluated by static water contact angles, X-ray photoelectron spectroscopy, and IR spectroscopy. Monolayers prepared by thermal, UV light, or visible light initiation were compared. Additionally, the ability of infrared reflection-absorption spectroscopy to study organic monolayers on silicon was explored. A reaction mechanism is discussed on the basis of investigations of the reaction behavior of 1-alkenes with silicon wafers with varying types and levels of doping. Finally, a series of mixed monolayers derived from the mixed solutions of a 1-alkene and an ω-fluoro-1-alkene were investigated to reveal that the composition of the mixed monolayers was directly proportional to the molar ratio of the two compounds in the solutions.
Halogenation through Deoxygenation of Alcohols and Aldehydes
Chen, Jia,Lin, Jin-Hong,Xiao, Ji-Chang
supporting information, p. 3061 - 3064 (2018/05/28)
An efficient reagent system, Ph3P/XCH2CH2X (X = Cl, Br, or I), was very effective for the deoxygenative halogenation (including fluorination) of alcohols (including tertiary alcohols) and aldehydes. The easily available 1,2-dihaloethanes were used as key reagents and halogen sources. The use of (EtO)3P instead of Ph3P could also realize deoxy-halogenation, allowing for a convenient purification process, as the byproduct (EtO)3Pa?O could be removed by aqueous washing. The mild reaction conditions, wide substrate scope, and wide availability of 1,2-dihaloethanes make this protocol attractive for the synthesis of halogenated compounds.
Copper-Catalyzed Regioselective Hydroalkylation of 1,3-Dienes with Alkyl Fluorides and Grignard Reagents
Iwasaki, Takanori,Shimizu, Ryohei,Imanishi, Reiko,Kuniyasu, Hitoshi,Kambe, Nobuaki
supporting information, p. 9347 - 9350 (2015/08/06)
Copper complexes generated in situ from CuCl2, alkyl Grignard reagents, and 1,3-dienes play important roles as catalytic active species for the 1,2-hydroalkylation of 1,3-dienes by alkyl fluorides through C-F bond cleavage. The alkyl group is introduced to an internal carbon atom of the 1,3-diene regioselectively, thus giving rise to the branched terminal alkene product. Making the switch: A copper-hydride species, generated by the treatment of a copper salt with alkyl Grignard reagents, catalyzes the 1,2-hydroalkylation of 1,3-dienes by alkyl fluorides and Grignard reagents. The alkyl group of the alkyl fluoride is selectively introduced to an internal carbon atom of the 1,3-diene and the Grignard reagent acts as hydride source to give the branched terminal alkene, even in the presence of alkenes and alkynes.
