苯呋喃，此分子架構，在天然物和藥物中相當常見許多天然物分子皆具有相似的結構，例如從豆科植物萃取的補骨脂 1 (Psoralen），用來治療皮膚的疾病。主要結構為苯呋喃的苯溴馬隆 2 (Benzbromarone)，具有降低血液中尿酸濃度的功能，另外苯呋喃衍生物還具有許多其他的療效，像是抗真菌、治療高血壓等。因此；研究合成苯呋喃衍生物成為化學家的重要領域。本實驗室近期發展了簡單且有效率製備呋喃和萘呋喃衍生物的方法。本篇論文以相同的方式，丙烯基醋酸鹽分子和苯酚衍生物為起始物，製備苯呋喃，拓展此製備方式的廣適性，並用簡單且有效率的方式，得到高產率的苯呋喃產物。

利用本實驗開發的丙烯基醋酸鹽分子110，和苯酚衍生物為起始物，經過一系列的篩選後，苯酚衍生物115、123、124，以碳酸鍶為催化劑，氯仿為溶劑，得到產物苯呋喃衍生物，最佳產率為91%。

The structure of benzofuran are very common in natural compounds, for example, Psoralen 1 and Benzbromarone 2. And the molecules containing benzofuran scaffold have a wide range of biological activies. So it is important to develope synthesis of benzofuran. Recently, our lab have developed a simple and efficient way to synthesize furan and napthofuran. Herein, we use the same way to synthesize benzofuan with the phenol derivaties and allylic acetate as the starting material.

After extensive optimization studies, we used the phenol 115、123、124 and allylic acetates as the starting material catalized by cesium carbonate, and chloform as the solvent. The benzofuran derivatives (16 examples) were obtained with the highest yield 91%.

(1) Burgstahler, A. W. ; Worden, L. R. Org. Synth. 1966 46, 28.
(2) Perkin, W. H. , J. Chem. Soc. 1870, 23, 368–371.
(3) Fujimura, O. ; Fu, G. C.; Grubbs, R. H. J. Org. Chem. 1994, 59, 4029.
(4) Whitehead, A. ; Moore, J. D. ; Hanson, P. R. Tetrahedron Lett. 2003, 44, 4275.
(5) Hekking, K. F. W. ; Moelands, M. A. H. ; van Delft, F. L. ; Rutjes, F. P. J. T. J. Org. Chem. 2006, 71, 6444.
(6) Huanga, K. H. ; Lia, S. R. ; Wanga, Y. F. ; Lina, Y. L. ; Chena, Y. H. ; Tsaia, T. W. ; Yangc, C. H. and Wanga, E. C. J. Chinese Chem. Soc. 2005, 52, 159.
(7) van Otterlo, W. A. L.; Morgans, G. L. ; Madeley, L. G. ; Kuzvidza, S. ; Moleele, S. S. ; Thornton, N. ; de Koning, C. B. Tetrahedron 2005, 61, 7746.
(8) Terada, Y. ; Arisawa, M. ; Nishida, A. Angew. Chem., Int. Ed. Engl. 2004, 43, 4063.
(9) Fecik, R. A. ; Frank, K. E. ; Gentry, E. J. ; Mitscher, L. A. ; Shibata, M. Pure Appl.Chem. 1999, 71, 559.
(10) Boehm, T. L. ; Showalter, H. D. H. J. Org. Chem. 1996, 61,6498.
(11) Habermann, J. ; Ley, S. V. ; Smits, R. J. Chem. Soc. Perkin Trans. 1999, 2421.
(12) Fancelli, D. ; Fagnolba, M. C. ; Severino, D. and Bedeschi, A. Tetrahedron Letters, 1997, 38, 2311.
(13) Nakamura, I. ; Mizushima, Y. and Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 15022.
(14) Nakamura, M. ; Ilies, L. ; Otsubo, S. and Nakamura, E. Org. Lett. 2006, 8, 2803.
(15) Gabriele, B. ; Mancuso, R. ; Salerno, G. and Costa, M. J. Org. Chem. 2007, 72,9278.
(16) Komine, Y. ; Kamisawa, A. ; and Tanaka, K. Org. Lett. 2009, 11, 2361.
(17) Liu, Y. ; Qian, J. ; Lou, S. and Xu, Z. J. Org. Chem. 2010, 75, 6300.
(18) Yagoubi, M. ; Cruz, A. C. F. ; Nichols, P. L. ; Elliott, R. L. and Willis, M. C. Angew. Chem. Int. Ed. 2010, 49,7958.
(19) Ye, S. ; Li, G. ; Pu, S. and Wu, J. Org. Lett. 2010, 14, 70.
(20) Huang, X. C. ; Liu, Y. L. ; Liang, Y. ; Pi, S. F. ; Wang, F. and
Li, J. H. Org. Lett., 2008, 10, 1525.
(21) Wang, S. ; Li, P. ; Yu, L. and Wang, L. , Org. Lett. 2011, 13, 5968.
(22) Arias, L. ; Vara, Y. and Cossio, F. P. , J. Org. Chem. 2012, 77(1), 266.