Citation:
	            
		            Zheng-Le  Zhao, Qing  Gu, Xin-Yan  Wu, Shu-Li  You. Pd(0)-catalyzed benzylation of indole through η3-benzyl palladium intermediate[J]. Chinese Journal of Catalysis,
							;2015, 36(1): 15-18.
						
							doi:
								10.1016/S1872-2067(14)60191-1
						
					
				
					
				
	        
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	                	An efficient method has been developed for the Pd(0)-catalyzed benzylation of indoles, which occurred with exclusive regioselectivity. When this reaction was performed in the presence of Pd(PPh3)4, it provided access to a broad range of substituted indoles bearing diarylmethanes at their 3-position in 90%-99% yields under mild conditions.
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								Keywords:
								
 - Benzylation,
 - Indole,
 - Triarylmethane,
 - η3-Benzyl palladium intermediate
 
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                    [1]
                
			
[1] Tsuji J. Palladium Reagents and Catalysts. Chichester: John Wiley & Sons, 2004. 431
 - 
			
                    [2]
                
			
[2] Zhang X, Feng X J, Liu H S, Qin Y H, Dai Y. Chin J Catal (张新, 冯秀娟, 刘鹤松, 秦余虎, 戴耀. 催化学报), 2012, 33: 523
 - 
			
                    [3]
                
			
[3] Kuwano R, Kondo Y, Matsuyama Y. J Am Chem Soc, 2003, 125: 12104
 - 
			
                    [4]
                
			
[4] Kuwano R, Kondo Y. Org Lett, 2004, 6: 3545
 - 
			
                    [5]
                
			
[5] Ueno S, Komiya S, Tanaka T, Kuwano R. Org Lett, 2012, 14: 338
 - 
			
                    [6]
                
			
[6] Trost B M, Czabaniuk L C. J Am Chem Soc, 2010, 132: 15534
 - 
			
                    [7]
                
			
[7] Mukai T, Hirano K, Satoh T, Miura M. Org Lett, 2010, 12: 1360
 - 
			
                    [8]
                
			
[8] Legros J Y, Toffano M, Fiaud J C. Tetrahedron: Asymmetry, 1995, 6: 1899
 - 
			
                    [9]
                
			
[9] Trost B M, Czabaniuk L C. J Am Chem Soc, 2012, 134: 5778
 - 
			
                    [10]
                
			
[10] Trost B M, Czabaniuk L C. Chem Eur J, 2013, 19: 15210
 - 
			
                    [11]
                
			
[11] Legros J Y, Primault G, Toffano M, Rivière M A, Fiaud J C. Org Lett, 2000, 2: 433
 - 
			
                    [12]
                
			
[12] Yokogi M, Kuwano R. Tetrahedron Lett, 2007, 48: 6109
 - 
			
                    [13]
                
			
[13] Assié M, Meddour A, Fiaud J C, Legros J Y. Tetrahedron: Asymmetry, 2010, 21: 1701
 - 
			
                    [14]
                
			
[14] Fields W H, Chruma J J. Org Lett, 2010, 12: 316
 - 
			
                    [15]
                
			
[15] Torregrosa R R P, Ariyarathna Y, Chattopadhyay K, Tunge J A. J Am Chem Soc, 2010, 132: 9280
 - 
			
                    [16]
                
			
[16] Blessley G, Holden P, Walker M, Brown J M, Gouverneur V. Org Lett, 2012, 14: 2754
 - 
			
                    [17]
                
			
[17] Bao M, Nakamura H, Yamamoto Y. J Am Chem Soc, 2001, 123: 759
 - 
			
                    [18]
                
			
[18] Ariafard A, Lin Z Y. J Am Chem Soc, 2006, 128: 13010
 - 
			
                    [19]
                
			
[19] Lu S R, Xu Z W, Bao M, Yamamoto Y. Angew Chem Int Ed, 2008, 47: 4366
 - 
			
                    [20]
                
			
[20] Peng B, Feng X J, Zhang X, Ji L Y, Bao M. Tetrahedron, 2010, 66: 6013
 - 
			
                    [21]
                
			
[21] Peng B, Feng X J, Zhang X, Zhang S, Bao M. J Org Chem, 2010, 75: 2619
 - 
			
                    [22]
                
			
[22] Peng B, Zhang S, Yu X Q, Feng X J, Bao M. Org Lett, 2011, 13: 5402
 - 
			
                    [23]
                
			
[23] Feng X J, Sun A L, Zhang S, Yu X Q, Bao M. Org Lett, 2013, 15: 108
 - 
			
                    [24]
                
			
[24] Zhang X, Feng X J, Yu X Q, He R, Bao M. Org Biomol Chem, 2013, 11: 4016
 - 
			
                    [25]
                
			
[25] Feng X J, Song J L, Liu H S, Wang L G, Yu X Q, Bao M. RSC Adv, 2013, 3: 18985
 - 
			
                    [26]
                
			
[26] Zhang S, Wang Y, Feng X J, Bao M. J Am Chem Soc, 2012, 134: 5492
 - 
			
                    [27]
                
			
[27] Zhang S, Bao M. Synlett, 2012, 23: 2431
 - 
			
                    [28]
                
			
[28] Kuwano R, Kusano H. Org Lett, 2008, 10: 1979
 - 
			
                    [29]
                
			
[29] Kuwano R, KondoY, Shirahama T. Org Lett, 2005, 7: 2973
 - 
			
                    [30]
                
			
[30] Johns A M, Tye J W, Hartwig J F. J Am Chem Soc, 2006, 128: 16010
 - 
			
                    [31]
                
			
[31] Kuwano R. Synthesis, 2009: 1049
 - 
			
                    [32]
                
			
[32] Zhu Y, Rawal V H. J Am Chem Soc, 2012, 134: 111
 - 
			
                    [33]
                
			
[33] Lakhdar S, Westermaier M, Terrier F, Goumont R, Boubaker T, Ofial A R, Mayr H. J Org Chem, 2006, 71: 9088
 - 
			
                    [34]
                
			
[34] Skurydina D F, Tolkachev V N, Zenkina D I, Nikolaeva T G, Tolkachev O N. Pharm Chem J, 2008, 42: 443
 - 
			
                    [35]
                
			
[35] Duxbury D F. Chem Rev, 1993, 93: 381
 - 
			
                    [36]
                
			
[36] Shchepinov M S, Korshun V A. Chem Soc Rev, 2003, 32: 170
 - 
			
                    [37]
                
			
[37] Nair V, Thomas S, Mathew S C, Abhilash K G. Tetrahedron, 2006, 62: 6731
 - 
			
                    [38]
                
			
[38] He Q L, Sun F L, Zheng X J, You S L. Synlett, 2009: 1111
 - 
			
                    [39]
                
			
[39] Sun F L, Zheng X J, Gu Q, He Q L, You S L. Eur J Org Chem, 2010: 47
 - 
			
                    [40]
                
			
[40] Wu K, Jiang Y J, Fan Y S, Sha D, Zhang S Q. Chem Eur J, 2013, 19: 474
 - 
			
                    [41]
                
			
[41] Pape A R, Kaliappan K P, Kündig E P. Chem Rev, 2000, 100: 2917
 - 
			
                    [42]
                
			
[42] Roche S P, Porco J A Jr. Angew Chem Int Ed, 2011, 50: 4068
 - 
			
                    [43]
                
			
[43] Zhuo C X, Zhang W, You S L. Angew Chem Int Ed, 2012, 51: 12662
 - 
			
                    [44]
                
			
[44] Zhuo C X, Zheng C, You S L. Acc Chem Res, 2014, 47: 2558
 
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