- Atom-efficient transition-metal-free arylation ofN,O-acetals using diarylzinc reagents through Zn/Zn cooperativity
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Exploiting the cooperative action of Lewis acid Zn(C6F5)2with diarylzinc reagents, the efficient arylation ofN,O-acetals to access diarylmethylamines is reported. Reactions take place under mild reaction conditions without the need for transtion-metal catalysis. Mechanistic investigations have revealed that Zn(C6F5)2not only acts as a Lewis acid activator, but also enables the regeneration of nucleophilic ZnAr2species, allowing a limiting 50 mol% to be employed.
- Borys, Andryj M.,Gil-Negrete, Jose M.,Hevia, Eva
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p. 8905 - 8908
(2021/09/10)
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- Phosphine-Borane Frustrated Lewis Pairs Derived from a 1,1′-Disubstituted Ferrocene Scaffold: Synthesis and Hydrogenation Catalysis
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(Dimesitylphosphino)ferrocene (FcPMes2) (1) reacted with HB(C6F5)2 (2 equiv) by disproportionation to give adduct FcPMes2·H2B(C6F5) (4) plus B(C6F5)3, whereas 1-(dimesitylphosphino)-1′-vinylferrocene (2) was cleanly hydroborated with HB(C6F5)2 to afford [Fe(??5-C5H4PMes2)(??5-C5H4CH2CH2B(C6F5)2)] (7). Compound 7 adopted an open non-interacting P/B frustrated Lewis pair (FLP) structure in the crystal state as well as in a solution. This frustrated Lewis pair heterolytically cleaved dihydrogen under mild conditions to give the respective zwitterionic [P]H+/[B]H- phosphonium/hydroborate product, [Fe(??5-C5H4PHMes2){??5-C5H4CH2CH2BH(C6F5)2}] (8), which served as a catalyst for the hydrogenation of the electron-rich ?€-systems (imine, enamine) as well as the electron-deficient carbon-carbon double and triple bonds in some enones and an ynone under more forcing conditions (50 bar H2 pressure, 50 °C).
- Jian, Zhongbao,Krupski, Sergei,?koch, Karel,Kehr, Gerald,Daniliuc, Constantin G.,Císa?ová, Ivana,?těpni?ka, Petr,Erker, Gerhard
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p. 2940 - 2946
(2017/08/21)
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- A Synthesis of α-Substituted Amines
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The reaction of amides with organolithium reagents followed by hydride reducing agents has been studied as a synthetic route to α-substituted amines.The stereochemistry of the amine has been observed to depend upon the nature of the reducing agent.
- Hwang, Yuing C.,Chu, Min,Fowler, Frank W.
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p. 3885 - 3890
(2007/10/02)
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