- An Atom-Economical Route to Substituted β-Arylethyl Ketones: Phosphomolybdic Acid-Catalyzed Carbohydroxylation of Terminal Alkynes in Organic Carbonate
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A highly efficient and atom-economical route for the synthesis of substituted β-arylethyl ketones was developed by using cheap phosphomolybdic acid (H3PMo12O40) as catalyst and non-volatile propylene carbonate (PC) as green solvent via the carbohydroxylation of terminal alkynes with benzylic alcohols under mild conditions. Various functional groups on the benzylic alcohols and terminal alkynes were tolerated, giving the corresponding substituted β-arylethyl ketones as products in good to excellent yields (up to 95%). It is worth noting that a turnover number (TON) of up to 520 was achieved in the protocol. The mechanism investigation showed that PC might stabilize the heteropoly anion and the carbocation intermediate thus facilitating the carbohydroxylation reaction. (Figure presented.).
- Yang, Guo-Ping,Zhang, Nan,Ma, Nuan-Nuan,Yu, Bing,Hu, Chang-Wen
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p. 926 - 932
(2017/03/27)
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- Catalytic C-C bond formation using triorganothallium reagents
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The first catalytic system employing triorganothallium compounds in the formation of carbon-carbon bonds, is described.
- Marko,Kantam
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p. 2255 - 2258
(2007/10/02)
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- Photolysis of 1,1,1-Triarylalk-2-enes and 1,1,1-Triarylhept-2-ynes. A Novel Generation of Aryl(alk-1-enyl)carbenes ans Aryl(alk-1-ynyl)carbenes
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Upon UV irradiation in methanol, 1,1,1-triarylhept-2-ynes underwent an α,α-elimination of two aryl groups to give a biaryl and the corresponding carbene which reacted with methanol to give a 1-aryl-1-methoxyhept-2-yne. 1,1,1-Triphenylalk-2-enes underwent α,α-elimination of two phenyl groups and also elimination of an alkene and a phenyl group to give biphenyl and a 1-phenylalkene respectively.In both cases, the corresponding carbenes were formed and were isolated as methanol insertion products (a 1-methoxy-1-phenylalk-2-ene and diphenylmethyl methyl ether, respectively).A rearrangement product, a 1,1,2-triphenylcyclopropane, was also formed.
- Shi, Min,Shouki, Kouji,Okamoto, Yoshiki,Takamuku, Setsuo
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p. 2443 - 2450
(2007/10/02)
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