- Cyano-borrowing reaction: Nickel-catalyzed direct conversion of cyanohydrins and aldehydes/ketones to β-cyano ketone
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A direct nickel-catalyzed, high atom- and step-economical reaction of cyanohydrins with aldehydes or ketones via an unprecedented "cyano-borrowing reaction" has been developed. Cleavage of the C-CN bond of cyanohydrins followed by aldol condensation and conjugate addition of cyanide to α,β-unsaturated ketones proceeded to deliver a range of racemic β-cyano ketones with good to high yields. The practical procedure with the use of a commercial and less-toxic CN source bodes well for wide application of this protocol.
- Li, Zhao-Feng,Li, Qian,Ren, Li-Qing,Li, Qing-Hua,Peng, Yun-Gui,Liu, Tang-Lin
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p. 5787 - 5792
(2019/06/17)
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- Conjugate Hydrocyanation of Chalcone Derivatives Using Ethyl Cyanoacetate as an Organic Cyanide Source
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The conjugate hydrocyanation of chalcone derivatives using ethyl cyanoacetate as an organic cyanide source at room temperature under open air and transition metal-free conditions was described. The protocol has advantages of using relatively cheap, less toxic, stable and easy-to-handle cyanating reagent, high yield, and mild reaction condition.
- Li, Zheng,Yin, Junjun
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p. 1179 - 1184
(2017/07/24)
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- Conjugate hydrocyanation of aromatic enones using potassium hexacyanoferrate(II) as an eco-friendly cyanide source
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A selective conjugate hydrocyanation of aromatic enones by a one-pot, two-step procedure using potassium hexacyanoferrate(II) as an original eco-friendly cyanide source, potassium hydroxide as a base, and benzoyl chloride as a promoter was described. This protocol has the advantages of a nontoxic cyanide source, high yield, and simple workup procedure. Georg Thieme Verlag Stuttgart · New York.
- Li, Zheng,Liu, Chenhui,Zhang, Yupeng,Li, Rongzhi,Ma, Ben,Yang, Jingya
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supporting information
p. 2567 - 2571
(2012/11/13)
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- Cyanation of α,β-unsaturated enones by malononitrile in open air under metal-catalyst-free conditions
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Cyanation of α,β-unsaturated enones by employing malononitrile as the organic cyanation source has been disclosed, which proceeds efficiently at room temperature in open air under metal-catalyst-free conditions. The Royal Society of Chemistry 2012.
- Lin, Shaoxia,Wei, Ying,Liang, Fushun
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supporting information
p. 9879 - 9881
(2012/11/07)
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- An efficient conjugate hydrocyanation of chalcones and related enones with TMSCN under solvent- and additive-free microwave conditions
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A first example of solvent- and additive-free 1,4-addition reaction of α,β-unsaturated ketones such as chalcones, 3-nonen-2-one and benzalacetone with trimethylsilyl cyanide (TMSCN) is described. The addition of TMSCN to chalcones, 3-nonen-2-one, and benzalacetone under microwave irradiation in the absence of Lewis or Br?nsted acids and solvents, yielded the corresponding β-cyanoketones in good to moderate yields, as quite rapidly as in 5 min. No systematic substituent effect of chalcones on the yields was observed. No reaction of α,β-unsaturated esters such as methyl cinnamate with TMSCN took place under the same conditions.
- Iida, Hirokazu,Moromizato, Tatsuya,Hamana, Hiroshi,Matsumoto, Kiyoshi
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p. 2037 - 2039
(2007/10/03)
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