Synthesis of N,N-diallylanilines by the reaction of anilines and allyl bromide in the presence of Mg–Al hydrotalcites at ambient temperature

References

• Li , L. and Jones , W.D. 2007 . Mechanistic Investigation of the Cobalt-Catalyzed Selective Conversion of Diallylanilines to Quinoline Involving C–N and C–H Activations . J. Am. Chem. Soc. , 129 : 10707 – 10713 .
   PubMed Web of Science ®Google Scholar
• Yang , S. and Chung , W. 1999 . Palladium Catalyzed N-Allylation of Anilines by Direct Use of Allyl Alcohols in the Presence of Titanium (IV) Isopropoxide . Tetrahedron Lett. , 40 : 953 – 956 .
   Web of Science ®Google Scholar
• Adak , L. , Chattopadhyay , K. and Ranu , B.C. 2009 . Palladium Nanoparticle-Catalyzed C-N bond Formation. A Highly Regio- and Streoselective Allylic Amination by Allyl Acetates . J. Org. Chem. , 74 : 3983 – 3985 .
   Web of Science ®Google Scholar
• Li , L. and Jones , W.D. 2007 . Mechanistic Investigation of the Cobalt-Catalyzed Selective Conversion of Diallylanilines to Quinoline Involving C–N and C–H activations . J. Am. Chem. Soc. , 129 : 10707 – 10713 .
   PubMed Web of Science ®Google Scholar
• Singh , C.B. ; Kavala , V. ; Samal , A.K. ; Patel , B.K. Aqueous-Mediated N-Alkylation of Amines . Eur. J. Org. Chem . 2007 , 1369 – 1377 .
   Web of Science ®Google Scholar
• Barluenga , J. , Najera , C. and Yus , M. A . 1980 . Convenient Synthesis of Substituted Piperazines via Aminomercuration-Demercuration of Diallylamines . J. Heterocycl. Chem. , 17 : 917 – 921 .
   Web of Science ®Google Scholar
• Ghosh , D. , Thander , L. , Ghosh , S.K. and Chattopadhyay , S.K. 2008 . Sequential Aza-Claisen Rearrangement and Ring-Closing Metathesis as a Route to 1-Benzazepine Derivatives . Synlett. , 19 : 3011 – 3015 .
   Google Scholar
• Onaka , M. , Umezono , A. , Kawai , M. and Izumi , Y. 1985 . N-Alkylation of Aniline Derivatives by Use of Potassium Cation-Exchanged Y-Type Zeolite . J. Chem. Soc. Chem. Commun. , 17 : 1202 – 1203 .
   Google Scholar
• Martinez , V. , Blais , J.-C. and Astruc , D. 2002 . General Route from Simple Methyl, Alkyl, and Cycloalkyl Arenes to Polycyclic Cyclopentenyl Aryl Derivatives. The CpFe Group as an Activator and Tag . Org. Lett. , 4 : 651 – 654 .
   PubMed Web of Science ®Google Scholar
• Ohshima , T. , Miyamoto , Y. , Ipposhi , J. , Nakahara , Y. , Utsunomiya , M. and Mashima , K. 2009 . Platinum-Catalyzed Direct Amination of Allylic Alcohols Under Mild Conditions: Ligand and Microwave Effects, Substrate Scope, and Mechanistic Study . J. Am. Chem. Soc. , 131 : 14317 – 14328 .
   PubMed Web of Science ®Google Scholar
• Utsunomiya , M. , Miyamoto , Y. , Ipposhi , J. , Ohshima , T. and Mashima , K. 2007 . Direct Use of Allylic Alcohols for Platinum-Catalyzed Monoallylation of Amines . Org. Lett. , 9 : 3371 – 3374 .
   PubMed Web of Science ®Google Scholar
• Barluenga , J. , Perez-Prieto , J. and Asensio , G. 1990 . Catalytic Aminomercuration of Olefins in a Tandem Aminomercuration-Deoxymercuration; One-Step Synthesis of Secondary n-Arylallylamines from Allylalcohols . Tetrahedron. , 46 : 2453 – 2460 .
   Web of Science ®Google Scholar
• Ozawa , F. , Okamoto , H. , Kawagishi , S. , Yamamoto , S. , Minami , T. and Yoshifuji , M. 2002 . (π-Allyl)Palladium Complexes Bearing Diphosphinidene-Cyclobutene Ligands (DPCB): Highly Active Catalysts for Direct Conversion of Allylic Alcohols . J. Am. Chem. Soc. , 124 : 10968 – 10969 .
   PubMed Web of Science ®Google Scholar
• Tao , Y. , Zhou , Y. , Qu , J. and Hidai , M. 2010 . Highly Ef?cient and Regioselective Allylic Amination of Allylic Alcohols Catalyzed by [Mo3PdS4] Cluster . Tetrahedron Lett. , 51 : 1982 – 1984 .
   Web of Science ®Google Scholar
• Kimura , M. , Futamata , M. , Shibata , K. and Tamaru , Y. 2003 . Pd·Et3B-Catalyzed Alkylation of Amines with Allylic Alcohols . Chem. Commun. , 2 : 234 – 235 .
   PubMed Web of Science ®Google Scholar
• Yang , S. and Chung , W. 1999 . Palladium Catalyzed N-Allylation of Anilines by Direct Use of Allyl Alcohols in the Presence of Titanium (IV) Isopropoxide . Tetrahedron Lett. , 40 : 953 – 956 .
   Web of Science ®Google Scholar
• Kayaki , Y. , Koda , T. and Ikariya , T. 2004 . Halide-Free Dehydrative Allylation Using Allylic Alcohols Promoted by a Palladium Triphenyl Phosphite Catalyst . J. Org. Chem , 69 : 2595 – 2597 .
   PubMed Web of Science ®Google Scholar
• Basu , B. , Paul , S. and Nanda , A.K. 2009 . Highly Selective N-Alkylation of Amines Promoted on Silica: An Ef?cient and Recyclable Surface . Green Chem. , 11 : 1115 – 1120 .
   Web of Science ®Google Scholar
• Shen , J. , Tu , M. and Hu , C. 1998 . Structural and Surface Acid/Base Properties of Hydrotalcite-Derived MgAlO Oxides Calcined at Varying Temperatures . J. Solid State Chem. , 137 : 295
   Web of Science ®Google Scholar
• Sels , F.B. , Vos , D.E. De. and Jacobs , P.A. 2001 . Hydrotalcite-Like Anionic Clays in Catalytic Organic Reactions . Catal. Rev. , 43 : 443
   Web of Science ®Google Scholar
• Cavani , F. , Trifiro , F. and Vaccari , A. 1991 . Hydrotalcite-Type Anionic Clays: Preparation, Properties and Applications . Catal. Today. , 11 : 173
   Web of Science ®Google Scholar
• Kang , K.H. , Choi , K. , Koh , H.Y. , Kim , Y. , Chung , B.Y. and Cho , Y.S. 2001 . Indium Mediated Allylation of Nitro Group on Nitrobenzene Derivatives in Aqueous Media . Synth. Commun. , 31 : 2277 – 2286 .
   Web of Science ®Google Scholar
• Nakagawa , H. , Hirabayashi , T. , Sakaguchi , S. and Ishii , Y. 2004 . Allylation of Alcohols and Carboxylic Acids with Allyl Acetate Catalyzed by [Ir(cod)2] + BF4- Complex . J. Org. Chem. , 69 : 3474 – 3477 .
   PubMed Web of Science ®Google Scholar