- Selective Synthesis of Carbonates from Glycerol, CO 2, and Alkyl Halides Using tert -Butyltetramethylguanidine
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Herein, we describe the guanidine-promoted synthesis of carbonates from glycerol, CO 2, and alkyl halides. Specifically, a linear tricarbonate (1,2,3-tri- O -butoxycarbonylglycerol), a dicarbonate [butyl (2-oxo-1,3-dioxolan-4-yl)methyl carbonate] containing a linear and a cyclic moiety, and a cyclic monocarbonate (4-hydroxymethyl-2-oxo-1,3-dioxolan) were selectively obtained in good yields, which were strongly affected by the steric bulkiness of the guanidine group substituents. The developed method exhibits the advantages of high efficiency and mild conditions, thus being a powerful tool for the synthesis of value-added products from industrial by-products.
- Mihara, Masatoshi,Moroga, Kaname,Iwasawa, Tetsuo,Nakai, Takeo,Ito, Takatoshi,Ohno, Toshinobu,Mizuno, Takumi
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supporting information
p. 1759 - 1764
(2018/07/21)
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- Guanidine/Pd(OAc)2-catalyzed room temperature Suzuki cross-coupling reaction in aqueous media under aerobic conditions
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(Chemical Equation Presented) A highly efficient Pd(OAc) 2/guanidine aqueous system for the room temperature Suzuki cross-coupling reaction has been developed. The new water-soluble and air-stable catalyst Pd(OAc)2·(1f)2 from Pd-(OAc)2 and 1,1,3,3-tetramethyl-2-n-butylguanidine (1f) was synthesized and characterized by X-ray crystallography. In the presence of Pd(OAc) 2·(1f)2, coupling of arylboronic acids with a wide range of aryl halides, including aryl iodides, aryl bromides, even activated aryl chlorides, was carried out smoothly in aqueous solvent to afford the cross-coupling products in good to excellent yields and high turnover numbers (TONs) (TONs up to 850 000 for the reaction of 1-iodo-4-nitrobenzene and phenylboronic acid). Furthermore, this mild protocol could tolerate a broad range of functional groups.
- Li, Shenghai,Lin, Yingjie,Cao, Jungang,Zhang, Suobo
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p. 4067 - 4072
(2008/02/04)
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- Synthesis and Properties of a Series of Sterically Hindered Guanidine Bases
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By the reaction of Vilsmeier salts, derived from tetra-alkylureas or from tetra-alkylthioureas, with primary aliphatic amines, a series of sterically hindered penta-alkyl guanidines has been prepared. 2-t-Butyl-1',1',3'',3''-tetramethylguanidine and pentaisopropylguanidine combine ease of preparation with a range of resistance to alkylating agents.Preliminary experiments indicate that these inexpensive bases will useful in organic synthesis.
- Barton, Derek H. R.,Elliott, John D.,Gero, Stephan D.
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p. 2085 - 2090
(2007/10/02)
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- The Synthesis and Properties of a Series of Strong but Hindered Organic Bases
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A series of highly hindered N1,N2,N2,N3,N3-penta-alkylguanidines has been synthesised from inexpensive starting materials; these strong bases show interesting effects in organic synthesis.
- Barton, Derek H. R.,Elliott, John D.,Gero, Stephen D.
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p. 1136 - 1137
(2007/10/02)
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