An efficient hydrocyanation of α, β-unsaturated diesters with TMSCN catalyzed by MgI₂ etherate

References

• Carruthers, W.; Coldham, I. Modern Methods of Organic Synthesis, 4th ed.; Cambridge University Press: Cambridge, 2004.
   Google Scholar
• (a) Kawai, H.; Okusu, S.; Tokunaga, E.; Sato, H.; Shiro, M.; Shibata, N. Organocatalytic Asymmetric Synthesis of Trifluoromethyl‐Substituted Diarylpyrrolines: Enantioselective Conjugate Cyanation of β‐Aryl‐β‐Trifluoromethyl‐Disubstituted Enones. Angew. Chem. Int. Ed. Engl. 2012, 51, 4959–4962. DOI: 10.1002/anie.201201278;.(b) Provencher, B. A.; Bartelson, K. J.; Liu, Y.; Foxman, B. M.; Deng, L. Structural Study‐Guided Development of Versatile Phase‐Transfer Catalysts for Asymmetric Conjugate Additions of Cyanide. Angew. Chem. Int. Ed. Engl. 2011, 50, 10565–10569. DOI: 10.1002/anie.201105536; (c) Kawasaki, Y.; Fujii, A.; Nakano, Y.; Sakaguchi, S.; Ishii, Y. Acetylcyanation of Aldehydes with Acetone Cyanohydrin and Isopropenyl Acetate by Cp*2Sm (thf)2. J. Org. Chem. 1999, 64, 4214–4216. DOI: 10.1021/jo990030o.
   PubMed Web of Science ®Google Scholar
• Wang, Y. -F.; Zeng, W.; Sohail, M.; Guo, J.; Chen, F. Highly Efficient Asymmetric Conjugate Hydrocyanation of Aromatic Enones by an Anionic Chiral Phosphate Catalyst. Eur. J. Org. Chem. 2013, 4624–4633. DOI: 10.1002/ejoc.201300406.
   Web of Science ®Google Scholar
• Tanaka, Y.; Kanai, M.; Shibasaki, M. A Catalytic Enantioselective Conjugate Addition of Cyanide to Enones. J. Am. Chem. Soc. 2008, 130, 6072–6073. DOI: 10.1021/ja801201r.
   PubMed Web of Science ®Google Scholar
• (a) Zhang, J.; Liu, X.; Wang, R. Magnesium Complexes as Highly Effective Catalysts for Conjugate Cyanation of α, β‐Unsaturated Amides and Ketones. Chem. Eur. J. 2014, 20, 4911–4915. DOI: 10.1002/chem.201304835; (b) Kurono, N.; Nii, N.; Sakaguchi, Y.; Uemura, M.; Ohkuma, T. Asymmetric Hydrocyanation of α, β‐Unsaturated Ketones into β‐Cyano Ketones with the [Ru(phgly)2(binap)]/C6H5OLi Catalyst System. Angew. Chem. Int. Ed. Engl. 2011, 50, 5541–5544. DOI: 10.1002/anie.201100939; (c) Jingya, Y.; Fuxue, C. Highly Efficient Syntheses of β-Cyanoketones via Conjugate Addition of Me3SiCN to Aromatic Enones. Chin. J. Chem. 2010, 28, 981–987. DOI: 10.1002/cjoc.201090182; (d) Tanaka, Y.; Kanai, M.; Shibasaki, M. Catalytic Enantioselective Construction of β-Quaternary Carbons via a Conjugate Addition of Cyanide to β, β-Disubstituted α, β-Unsaturated Carbonyl Compounds. J. Am. Chem. Soc. 2010, 132, 8862–8863. DOI: 10.1021/ja1035286; (e) Yang, J.; Wu, S.; Chen, F. -X. Chiral Sodium Phosphate Catalyzed Enantioselective 1, 4-Addition of TMSCN to Aromatic Enones. Synlett. 2010, 2725–2728. DOI: 10.1055/s-0030-1258817; (f) Yang, J.; Shen, Y.; Chen, F. X. Highly Efficient Cs2CO3-Catalyzed 1, 4-Addition of Me3SiCN to Enones with Water as the Additive. Synthesis 2010, 1325–1333. DOI: 10.1055/s-0029-1218653; (g) Yang, J.; Wang, Y.; Wu, S.; Chen, F. -X. The Highly Efficient 1, 4-Addition of TMSCN to Aromatic Enones Catalyzed by CsF with Water as the Additive. Synlett. 2009, 3365–3367. DOI: 10.1055/s-0029-1218376; (h) Tanaka, Y.; Kanai, M.; Shibasaki, M. Catalytic Conjugate Addition of Cyanide to Enones: Cooperative Catalysis of Ni (0) and Gd(OTf)3. Synlett. 2008, 2295–2298. DOI: 10.1055/s-2008-1078264
   PubMed Web of Science ®Google Scholar
• Ohkuma, T.; Kurono, N. Asymmetric Cyanation with the Chiral Ru–Li Combined Catalysts. Synlett. 2012, 1865–1881. DOI: 10.1055/s-0032-1316545.
   Web of Science ®Google Scholar
• Lin, S.; Wei, Y.; Liang, F. Cyanation of α, β-Unsaturated Enones by Malononitrile in Open Air Under Metal-catalyst-free Conditions. Chem. Commun. 2012, 48, 9879–9881. DOI: 10.1039/c2cc35528k.
   PubMed Web of Science ®Google Scholar
• (a) Li, Z.; Yin, J.; Li, T.; Wen, G.; Shen, X.; Yang, J. Regioselective 1, 4-Conjugate Hydrocyanation of Dienones using Potassium Hexacyanoferrate (II) as an Eco-friendly Cyanide Source. Tetrahedron 2014, 70, 5619–5625. DOI: 10.1016/j.tet.2014.06.079; (b) Li, Z.; Zhang, Y.; Li, R.; Ma, B. Yang, J. Conjugate Hydrocyanation of Aromatic Enones Using Potassium Hexacyanoferrate (II) as an Eco-friendly Cyanide Source. Synlett. 2012, 2567–2571. DOI: 10.1055/s-0032-1317179.
   Web of Science ®Google Scholar
• Pavia, C.; Ballerini, E.; Bivona, L. A.; Giacalone, F.; Aprile, C.; Vaccaro, L.; Gruttadauria, M. Palladium Supported on Cross‐Linked Imidazolium Network on Silica as Highly Sustainable Catalysts for the Suzuki Reaction under Flow Conditions. Adv. Synth. Catal. 2013, 355, 2007–2018. DOI: 10.1002/adsc.201300215.
   Web of Science ®Google Scholar
• Nandi, S.; Patel, P.; Jakhar, A.; Khan, N. H.; Biradar, A. V.; Kureshy, R. I.; Bajaj, H. C. Cucurbit [6] uril‐Stabilized Palladium Nanoparticles as a Highly Active Catalyst for Chemoselective Hydrogenation of Various Reducible Groups in Aqueous Media. Chem. Select 2017, 2, 9911–9919. DOI: 10.1002/slct.201702196.
   Google Scholar
• Yamamoto, K.; Komatsu, K. Purification and Characterization of Nitrilase Responsible for the Enantioselective Hydrolysis from Acinetobacter sp. AK 226. Agric. Bio. Chem. 1991, 55, 1459–1466. DOI: 10.1080/00021369.1991.10870831.
   PubMed Web of Science ®Google Scholar
• Jiang, D.; Wang, Y. Y.; Dai, L. Y. Esterification of Acetonitrile with Alcohols in Novel Brönsted Acidic Ionic Liquids. Catal. Lett. 2008, 95, 265–271. DOI: 10.1007/s11144-008-5345-8.
   Web of Science ®Google Scholar
• Kim, J. Y.; Livinghouse, T. Enantioselective Intramolecular Alkene Hydroaminations Catalyzed by Yttrium Complexes of Axially Chiral Bisthiolate Ligands. Org. Lett. 2005, 7, 1737–1739. DOI: 10.1021/ol050294z.
   PubMed Web of Science ®Google Scholar
• Fleming, F. F.; Yao, L.; Ravikumar, P. C.; Funk, L.; Shook, B. C. Nitrile-containing Pharmaceuticals: Efficacious Roles of the Nitrile Pharmacophore. J. Med. Chem. 2010, 53, 7902–7917. DOI: 10.1021/jm100762r.
   PubMed Web of Science ®Google Scholar
• Li, Z.; Zhang, Y.; Wen, F.; Yin, J.; Zheng, H.; Li, H.; Yang, J. Hydrocyanation of Arylidenemalonates Using Potassium Hexacyanoferrate(II) as an Eco-friendly cyanide source. J. Chem. Res. 2013, 37(10), 601–603. 67120737 DOI: 10.3184/174751913X137873.
   Google Scholar
• Li, P. C.; Zhang, Y. D.; Chen, Z. L.; Zhang, X. X. Highly Efficient Three-component Strecker-type Reaction Catalyzed by MgI2 Etherate Under Solvent-free Conditions. Tetrahedron Lett. 2017, 58, 1854–1858. DOI: 10.1016/j.tetlet.2017.03.087.
   Web of Science ®Google Scholar