Acryl Activation by Intramolecular Hydrogen Bond: Morita Baylis Hillman Reaction of Acrylamide with Broad Substrate Scope

作者: Kishor Chandra Bharadwaj

DOI: 10.1002/SLCT.201701081

关键词: Hydrogen bondIntramolecular forceBaylis–Hillman reactionAcrylamideAlkeneDABCOMichael reactionPolymer chemistryChemistry

摘要: Use of acrylamide as an activated alkene in largely recognized Morita Baylis Hillman (MBH) reaction has been least explored owing to less reactivity Michael acceptor. Contrary have profound applications synthetic, medicinal and polymer chemistry. An intramolecular Hydrogen bond activated, MBH N-(2-hydroxyphenyl) developed. With various control experiments, role ortho hydroxy was found be activator critical for success reaction. Under the influence DABCO, designed acrylamides gave wide substrate scope including a number reactive aldehydes chemo selective reactions. Such mode activation can helpful design other reactions too. example presented by successful addition

参考文章(86)
Deevi Basavaiah, Sutanuka Pal, Gorre Veeraraghavaiah, Kishor Chandra Bharadwaj, The Baylis–Hillman acetates as a source of ambiphilic molecules: a simple synthesis of 1,3-thiazinane-2-thione frameworks Tetrahedron. ,vol. 71, pp. 4659- 4664 ,(2015) , 10.1016/J.TET.2015.04.087
Yi-fei Ji, Hong Yan, Qi-bai Jiang, Effective Nitration of Anilides and Acrylamides by tert-Butyl Nitrite European Journal of Organic Chemistry. ,vol. 2015, pp. 2051- 2060 ,(2015) , 10.1002/EJOC.201403510
Masaki Nakahata, Yoshinori Takashima, Akira Harada, Highly Flexible, Tough, and Self-Healing Supramolecular Polymeric Materials Using Host-Guest Interaction Macromolecular Rapid Communications. ,vol. 37, pp. 86- 92 ,(2016) , 10.1002/MARC.201500473
F. Christopher Pigge, R. Dhanya, Erik R. Hoefgen, Morita–Baylis–Hillman Cyclizations of Arene–Ruthenium‐Functionalized Acrylamides Angewandte Chemie. ,vol. 46, pp. 2887- 2890 ,(2007) , 10.1002/ANIE.200605045
Abigail G. Doyle, Eric N. Jacobsen, Small-molecule H-bond donors in asymmetric catalysis. Chemical Reviews. ,vol. 107, pp. 5713- 5743 ,(2007) , 10.1021/CR068373R
Le Du, Peng Cao, Junwei Xing, Yazhou Lou, Liyin Jiang, Liangchun Li, Jian Liao, Hydrogen‐Bond‐Promoted Palladium Catalysis: Allylic Alkylation of Indoles with Unsymmetrical 1,3‐Disubstituted Allyl Acetates Using Chiral Bis(sulfoxide) Phosphine Ligands Angewandte Chemie. ,vol. 52, pp. 4207- 4211 ,(2013) , 10.1002/ANIE.201209485
Keith J. Winstanley, David K. Smith, Ortho-Substituted Catechol Derivatives: The Effect of Intramolecular Hydrogen-Bonding Pathways on Chloride Anion Recognition Journal of Organic Chemistry. ,vol. 72, pp. 2803- 2815 ,(2007) , 10.1021/JO0623989
Tian-Yu Liu, Min Xie, Ying-Chun Chen, Organocatalytic asymmetric transformations of modified Morita–Baylis–Hillman adducts Chemical Society Reviews. ,vol. 41, pp. 4101- 4112 ,(2012) , 10.1039/C2CS35017C