Transition metal-free S_NAr-type etherification with allyl alcohols: Synthesis of allyl pyridyl ethers

References

• Cristau, P.; Vors, J. P.; Zhu, J. Rapid and Diverse Route to Natural Product-like Biaryl Ether Containing Macrocycles. Tetrahedron 2003, 59, 7859–7870. DOI: 10.1016/j.tet.2003.08.031.
   Web of Science ®Google Scholar
• Thompson, A. M.; Sutherland, H. S.; Palmer, B. D.; Kmentova, I.; Blaser, A.; Franzblau, S. G.; Wan, B.; Wang, Y.; Ma, Z.; Denny, W. A. Synthesis and Structure-Activity Relationships of Varied Ether Linker Analogues of the Antitubercular Drug (6S)-2-Nitro-6-{[4-(Trifluoromethoxy)Benzyl]Oxy}-6,7-Dihydro-5h-Imidazo[2,1-b][1,3]Oxazine (PA-824). J. Med. Chem. 2011, 54, 6563–6585. DOI: 10.1021/jm200377r.
   PubMed Web of Science ®Google Scholar
• Li, W.; Du, L.; Li, M. Alkaloids and Flavonoids as α(1)-Adrenergic Receptor Antagonists. Curr. Med. Chem. 2011, 18, 4923–4932. DOI: 10.2174/092986711797535209.
   PubMed Web of Science ®Google Scholar
• Chen, S. W.; Wang, Y. H.; Jin, Y.; Tian, X.; Zheng, Y. T.; Luo, D. Q.; Tu, Y. Q. Synthesis and anti-HIV-1 Activities of Novel Podophyllotoxin Derivatives. Bioorg. Med. Chem. Lett. 2007, 17, 2091–2095. DOI: 10.1016/j.bmcl.2006.11.070.
   PubMed Web of Science ®Google Scholar
• Frlan, R.; Kikelj, D. Recent Progress in Diaryl Ether Synthesis. Synthesis 2006, 14, 2271–2285. DOI: 10.1055/s-2006-942440.
   Web of Science ®Google Scholar
• Thangapriya, C.; Ilaamirthamani, S.; Kumarraja, M. Highly Regioselective O-Allylation of Phenol Derivatives Using MMZ Cu(I)Y Catalyst. Synth. Commun. 2019, 50, 361–367. DOI: 10.1080/00397911.2019.1695838.
   Web of Science ®Google Scholar
• Yang, Q. Q.; Liu, N.; Yan, J. Y.; Ren, Z. L.; Wang, L. Visible Light‐ and Heat‐Promoted C − O Coupling Reaction of Phenols and Aryl Halides. Asian J. Org. Chem. 2020, 9, 116–120. DOI: 10.1002/ajoc.201900666.
   Web of Science ®Google Scholar
• Wu, Y. B.; Xiao, L.; Mao, C. L.; Zang, Z. L.; Zhou, C. H.; Cai, G. X. Regio‐ and Stereoselective Synthesis of Enynyl‐Aryl Ethers Enabled by Copper/Iodide Tandem Catalysis. Adv. Synth. Catal. 2019, 361, 4461–4467. DOI: 10.1002/adsc.201900626.
   Web of Science ®Google Scholar
• Chen, Z.; Jiang, Y.; Zhang, L.; Guo, Y.; Ma, D. Oxalic Diamides and Tert-Butoxide: Two Types of Ligands Enabling Practical Access to Alkyl Aryl Ethers via Cu-Catalyzed Coupling Reaction. J. Am. Chem. Soc. 2019, 141, 3541–3549. DOI: 10.1021/jacs.8b12142.
   PubMed Web of Science ®Google Scholar
• Ullmann, F. Ueber Eine Neue Darstellungsweise Von Phenyläthersalicylsäure. *Ber. Dtsch. Chem. Ges. 1904, 37, 853–854. DOI: 10.1002/cber.190403701141.
   Google Scholar
• Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. Novel Electron-Rich Bulky Phosphine Ligands Facilitate the Palladium-Catalyzed Preparation of Diaryl Ethers. J. Am. Chem. Soc. 1999, 121, 4369–4378. DOI: 10.1021/ja990324r.
   Web of Science ®Google Scholar
• Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. Palladium-Catalyzed C−O Coupling Involving Unactivated Aryl Halides. Sterically Induced Reductive Elimination to Form the C−O Bond in Diaryl Ethers. J. Am. Chem. Soc. 1999, 121, 3224–3225. DOI: 10.1021/ja984321a.
   Web of Science ®Google Scholar
• Williamson, A. W. XXII.—on Etherification. Q. J. Chem. Soc. 1852, 4, 229–239. DOI: 10.1039/QJ8520400229.
   Google Scholar
• Lindley, J. Tetrahedron Report Number 163. Tetrahedron 1984, 40, 1433–1456. DOI: 10.1016/S0040-4020(01)91791-0.
   Web of Science ®Google Scholar
• Aspinall, H. C.; Greeves, N.; Lee, W.-M.; McIver, E. G.; Smith, P. M. An Improved Williamson Etherification of Hindered Alcohols Promoted by 15-Crown-5 and Sodium Hydride. Tetrahedron Lett. 1997, 38, 4679–4682. DOI: 10.1016/S0040-4039(97)00965-9.
   Web of Science ®Google Scholar
• Rodrigues, A.; Lee, E. E.; Batey, R. A. Enantioselective Palladium(II)-Catalyzed Formal [3,3]-Sigmatropic Rearrangement of 2-Allyloxypyridines and Related Heterocycles. Org. Lett. 2010, 12, 260–263. DOI: 10.1021/ol9025759.
   PubMed Web of Science ®Google Scholar
• Strayer, T. A.; Culy, C. C.; Bunner, M. H.; Frank, A. R.; Albiniak, P. A. In Situ Synthesis of 2-Allyloxy-1-Methylpyridinium Triflate for the Allylation of Carboxylic Acids. Tetrahedron Lett. 2015, 56, 6807–6809. DOI: 10.1016/j.tetlet.2015.10.085.
   Web of Science ®Google Scholar
• Yang, J.; Guo, Y.; Wang, J.; Dudley, G. B.; Sun, K. DFT Study on the Reaction Mechanism and Regioselectivity for the [1,2]-Anionic Rearrangement of 2-Benzyloxypyridine Derivatives. Tetrahedron 2019, 75, 4451–4457. DOI: 10.1016/j.tet.2019.06.018.
   Web of Science ®Google Scholar
• Wang, F.; Wang, J.; Zhang, Y.; Yang, J. The [1,2]- and [1,4]-Wittig Rearrangement. Tetrahedron 2020, 76, 130857. DOI: 10.1016/j.tet.2019.130857.
   Web of Science ®Google Scholar
• Poon, K. W. C.; Dudley, G. B. Mix-and-Heat Benzylation of Alcohols Using a Bench-Stable Pyridinium Salt. J. Org. Chem. 2006, 71, 3923–3927. DOI: 10.1021/jo0602773.
   PubMed Web of Science ®Google Scholar
• Krähling, L.; Krey, J.; Jakobson, G.; Grolig, J.; Miksche, L. Allyl Compounds. Ullmann’s Encyclopedia of Industrial Chemistry. Wiley‐VCH: Weinheim, 2000.
   Google Scholar
• Amii, H.; Uneyama, K. C-F Bond Activation in Organic Synthesis. Chem. Rev. 2009, 109, 2119–2183. DOI: 10.1021/cr800388c.
   PubMed Web of Science ®Google Scholar
• Sokolov, A. V. Transition States in the Reaction of Radical Addition to the Vinyl Double Bond. Russ. Chem. Bull. 1993, 42, 640–644. DOI: 10.1007/BF00703996.
   Web of Science ®Google Scholar