- Titanium(III)-Catalyzed Reductive Decyanation of Geminal Dinitriles by a Non-Free-Radical Mechanism
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A titanium-catalyzed mono-decyanation of geminal dinitriles is reported. The reaction proceeds under mild conditions, tolerates numerous functional groups, and can be applied to quaternary malononitriles. A corresponding desulfonylation is demonstrated as well. Mechanistic experiments support a catalyst-controlled cleavage without the formation of free radicals, which is in sharp contrast to traditional stoichiometric radical decyanations. The involvement of two TiIII species in the C?C cleavage is proposed, and the beneficial role of added ZnCl2 and 2,4,6-collidine hydrochloride is investigated.
- Weweler, Jens,Younas, Sara L.,Streuff, Jan
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p. 17700 - 17703
(2019/11/13)
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- A one-pot electrophilic cyanation–functionalization strategy for the synthesis of disubstituted malononitriles
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Malononitriles are valuable synthetic intermediates for many applications, including the synthesis of herbicides and other biologically active molecules, and the synthesis of chiral ligands for asymmetric catalysis. This article describes the development of a procedure for the conversion of primary nitriles to malononitriles using dimethylmalononitrile, a commercial, non-toxic, carbon-bound source of electrophilic cyanide. This procedure avoids the use of toxic cyanide or malononitrile as a starting material. This protocol is further applied to the dicyanation of benzyl Grignard reagents, generated from benzyl bromides, yielding fully functionalized malononitriles from a nitrile-free precursor.
- Mills, L. Reginald,Rousseaux, Sophie A.L.
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p. 4298 - 4306
(2019/05/22)
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- Potassium tert -Butoxide Mediated Arylation of 2-Substituted Malononitriles Using Diaryliodonium Salts
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Direct arylation of 2-substituted malononitriles using diaryliodonium salts without involving transition-metal catalysts was developed. By using potassium tert -butoxide as a promoter, the desired 2-substituated α-arylmalononitriles derivatives were synthesized in good to excellent yields of 55-96%. This synthetic method provided an efficient way to prepare a variety of 2-substituted arylmalononitriles which were useful in agrochemicals.
- Han, Jianwei,Qian, Xiaofei,Xu, Bowen,Wang, Limin
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supporting information
p. 2139 - 2142
(2017/09/26)
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- MALONONITRILE COMPOUNDS FOR CONTROLLING ANIMAL PESTS
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The invention relates to the use of a compound of formula (I) or a salt thereof for combating animal pests, where the symbols and indices are defined in the specification.
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Page/Page column 184
(2014/05/24)
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