648433-39-0Relevant academic research and scientific papers
Rhodium-catalyzed allylation of benzyl acetates with allylsilanes
Onodera, Gen,Yamamoto, Eriko,Tonegawa, Shota,Iezumi, Makoto,Takeuchi, Ryo
scheme or table, p. 2013 - 2021 (2011/10/09)
Benzyl acetate reacted with allyltrimethylsilane to give an allylation product in the presence of a catalytic amount of the (cyclooctadiene)rhodium(I) chloride dimer {[Rh(cod)Cl]2}, sodium tetrakis[3,5- bis(trifluoromethyl)phenyl]borate (NaBARF), and triphenyl phosphite [P(OPh) 3] in refluxing 1,2-dichloroethane. Primary, secondary and tertiary benzyl acetates could be used for the reaction. Moreover, allylation of gem-benzyl acetate was possible with [Rh(cod)Cl]2, NaBARF, and P(OPh)3. Monoallylation and diallylation of gem-benzyl acetate could be controlled by altering the reaction conditions. Cationic rhodium species generated in situ act as a Lewis acid catalyst to give a benzyl carbocation by elimination of the acetoxy group from the benzylic carbon. Copyright
Catalytic coupling of N-benzylic sulfonamides with silylated nucleophiles at room temperature
Yang, Bai-Ling,Tian, Shi-Kai
supporting information; experimental part, p. 6180 - 6182 (2010/10/20)
In the presence of 2-10 mol% of Tf2NH, a range of N-benzylic sulfonamides smoothly react with allylic, propargylic, benzylic, or hydrido silanes at room temperature via sp3 carbon-nitrogen bond cleavage to afford structurally diverse products in moderate to excellent yields and with high chemo- and regioselectivity.
Copper(II)-catalyzed allylation of propargylic and allylic alcohols by allylsilanes: a facile synthesis of 1,5-enynes
Yadav,Subba Reddy,Srinivasa Rao,Raghavendra Rao
, p. 614 - 618 (2008/09/16)
Propargylic alcohols undergo smooth deoxygenative allylation with allylsilanes in the presence of a solution of 10 mol % of copper(II) tetrafluoroborate in acetonitrile to afford the corresponding 1,5-enynes in good to high yields under mild and neutral c
Synthesis of 1,5-enynes by Broonsted acid catalyzed substitution of propargylic alcohols and one-pot synthesis of bicyclo[3.1.0]hexenes
Sanz, Roberto,Martinez, Alberto,Miguel, Delia,Alvarez-Gutierrez, Julia M.,Rodriguez, Felix
, p. 3252 - 3256 (2008/09/16)
A practical air and moisture tolerant procedure for the preparation of 1,5-enynes from propargylic alcohols by the Bronsted acid catalyzed direct propargylic substitution of the hydroxy group with allylsilanes is described. Also, a straightforward sequent
BiCl3-catalyzed propargylic substitution reaction of propargylic alcohols with C-, O-, S- and N-centered nucleophiles
Zhan, Zhuang-Ping,Yang, Wen-Zhen,Yang, Rui-Feng,Yu, Jing-Liang,Li, Jun-Ping,Liu, Hui-Juan
, p. 3352 - 3354 (2008/09/19)
A general and efficient BiCl3-catalyzed substitution reaction of propargylic alcohols with carbon and heteroatom-centered nucleophiles such as allyl trimethylsilane, alcohols, aromatic compounds, thiols and amides, leading to the construction o
A general and efficient FeCl3-catalyzed nucleophilic substitution of propargylic alcohols
Zhan, Zhuang-Ping,Yu, Jing-Liang,Liu, Hui-Juan,Cui, Yuan-Yuan,Yang, Rui-Feng,Yang, Wen-Zhen,Li, Jun-Ping
, p. 8298 - 8301 (2007/10/03)
A general and efficient FeCl3-catalyzed substitution reaction of propargylic alcohols with carbon- and heteroatom-centered nucleophiles such as allyl trimethylsilane, alcohols, aromatic compounds, thiols, and amides, leading to the construction of C-C, C-O, C-S and C-N bonds, has been developed.
