Anhydride Induced One-Pot Synthesis of ortho-Acyloxy Diarylalkenes from 2-(1-Hydroxy-1-arylalkyl)phenols
- Corresponding author: Wang Feijun, feijunwang@ecust.edu.cn
	            Citation:
	            
		            Lü Wenwena, He Xinchuna, Shi Mina, Wang Feijun. Anhydride Induced One-Pot Synthesis of ortho-Acyloxy Diarylalkenes from 2-(1-Hydroxy-1-arylalkyl)phenols[J]. Chinese Journal of Organic Chemistry,
							;2019, 39(2): 532-537.
						
							doi:
								10.6023/cjoc201807024
						
					
				
					 
				
	        
 
	                
				Jain, N. K.; Krishnamurty, H. G. Indian J. Chem.,  Sect. B 2000,  39, 817.
										
				Arnone, A.; Modugno, V. D.; Nasini, G.; Pava, O. V. Gazz. Chim. Ital. 1990,  120, 397.
										
				Shaiq, A. M.; Shaukat, M.; Shaista, P.; Uddin, A. U.; Hafeez, G. Phytochemistry 1999,  50, 1385.
												 doi: 10.1016/S0031-9422(98)00480-4
											
										
				(a) Zheng, Y.-L.; Liu, Y.-Y.; Wu, Y.-M.; Wang, Y.-X. Lin, Y.-T.; Ye, M.-C. Angew. Chem., Int. Ed. 2016, 55, 6315.
 (b) Botteghi, C.; Corrias, T.; Marchetti, M.; Paganelli, S.; Piccolo, O. Org. Process Res. dev. 2002, 6, 379.
				(a) Zhang, Z.; Ju, T.; Miao, M.; Han, J.-L.; Zhang, Y.-H.; Zhu, X.-Y.; Ye, J.-H.; Yu, D.-J.; Zhi, Y.-G. Org. Lett. 2017, 19, 396.
 (b) Sasano, K.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2013, 135, 10954.
 (c) Li, J.-F.; Chang, W.-J.; Ren, W.-L.; Liu, W.; Wang, H.-N.; Shi, Y. Org. Biomol. Chem. 2015, 13, 10341.
				(a) Ghorai, J.; Reddy, A. C. S.; Anbarasan, P. Chem.-Eur. J. 2016, 22, 16042.
 (b) Yang, D.-J.; Zhu, Y.-F.; Yang, N.; Jiang, Q.-Q.; Liu, R.-H. Adv. Synth. Catal. 2016, 358, 1731.
 (c) Chang, M.-Y.; Huang, Y.-H.; Wang, H.-S. Tetrahedron 2016, 72, 3022.
				(a) Han, Y.-P.; Song, X.-R.; Qiu, Y.-F.; Li, X.-S.; Zhang, H.-R.; Zhu, X.-Y.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2016, 18, 3866.
 (b) Casanova, N.; Seoane, A.; MascareÇas, J. L.; Gulias, M. Angew. Chem., Int. Ed. 2015, 54, 2374.
				(a) Wang, Z.-B.; Ai, F.-J.; Wang, Z.; Zhao, W.-X.; Zhu, G.-G.; Lin, Z.-Y.; Sun, J.-W. J. Am. Chem. Soc. 2015, 137, 383.
 (b) Chen, J.-H.; Chen, C.-H.; Ji, C.-L.; Lu, Z. Org. Lett. 2016, 18, 1594.
				Nicolaou, K. C.; Snyder, S. A.; Huang, X.-H.; Simonsen, K. B.; Koumbis, A. E.; Bigot, A. J. Am. Chem. Soc. 2004, 126, 10162.
												 doi: 10.1021/ja040090y
											
										
				Kaswan, P.; Shelke, M. G.; Rao, K. V.; Kumar, A. Synlett 2016, 27, 2553.
												 doi: 10.1055/s-0035-1560559
											
										
				Wang, Z.-N.; He, X.-X.; Zhang, R.; Zhang, G.; Xu, G. X.; Zhang, Q.; Xiong, T.; Zhang, Q. Org. Lett. 2017,  19, 3067.
										
				Han, P.; Wang, R.-J.; Wang, D. Z. Tetrahedron 2011,  67, 8873.
												 doi: 10.1016/j.tet.2011.09.073
											
										
				Zhang, Q.; Zheng, G.-F.; Zhang, Q; Li, Y. J. Org. Chem. 2017, 82, 8258.
												 doi: 10.1021/acs.joc.7b01089
											
										
				Xie, J.; Li, J.; Weingand, V.; Rudolph, M.; Hashmi, A. S. K. Chem.-Eur. J. 2016,  22, 12646.
												 doi: 10.1002/chem.v22.36
											
										
				Moure, M. J.; Martin, R. S.; Dominguez, E. Angew. Chem.,  Int. Ed. 2012,  57, 3220.
										
				(a) Haldar, S.; Koner, S. Beilstein J. Org. Chem. 2013, 9, 49.
 (b) Tochigi, A.; Tsukamoto, K.; Suzuki, N.; Masuyama, Y. Eur. J. Org. Chem. 2016, 5678.
				Chang, M.-Y.; Huang, Y.-H.; Wang, H.-S. Tetrahedron 2016,  72, 3022.
												 doi: 10.1016/j.tet.2016.04.018
											
										
				Zou, Y.-J.; Qin, L.-N.; Ren, X.-F.; Lu, Y.-P.; Li, Y.-X.; Zhou, J.-R. Chem. Eur. J. 2013,  19, 3504.
												 doi: 10.1002/chem.201203646
											
										
				Berthiol, F.; Doucet, H.; Santelli, M. Eur. J. Org. Chem. 2003, 1091.
										
				Hamze, A.; Veau, D.; Provot, O.; Brion, J. D.; Alami, M. J. Org. Chem. 2009,  74, 1337.
												 doi: 10.1021/jo802460z
											
										
				Roche, M.; Hamze, A.; Provot, O.; Brion, J. D.; Alami, M. J. Org. Chem. 2013,  78, 445.
												 doi: 10.1021/jo3023268
											
										
				(a) Zhang, Y.; He, Y.; Li, L.-S.; Ji, M.-M.; Li, X.-Z.; Zhu, G.-G. J. Org. Chem. 2018, 83, 2898. 
 (b) Hu, F.-D.; Xia, Y.; Ye, F.; Liu, Z.-X.; Ma, C.; Zhang, Y.; Wang, J.-B. Angew. Chem., Int. Ed. 2014, 53, 1364.
				Sasano, K.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2013, 135,  10954.
												 doi: 10.1021/ja405503y
											
										
				(a) Brady, W. T.; Giang, Y. F. J. Org. Chem. 1985, 50, 5177.
 (b) Wang, Z.-B.; Ai, F.-J.; Wang, Z.; Zhao, W.-X.; Zhu, G.-Y.; Lin, Z.-Y.; Sun, Z.-W. J. Am. Chem. Soc. 2015, 137, 383.
 (c) Ogawa, N.; Yamaoka, Y.; Yamada, K.; Takasu, K. Org. Lett. 2017, 19, 3327.
				(a) Chiang, Y.; Jerry, K. A. Org. Biomol. Chem. 2004, 2, 1090.
 (b) Uchida, M.; Kuma, M.; Irie, M. Bull. Chem. Soc. Jpn. 1996, 69, 1023.
 (c) Guo, L.; Zhang, F.-Y.; Hu, W.-M.; Lia, L.; Jia, Y.-X. Chem. Commun. 2014, 50, 3299.
 (d) Sasano, K.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2013, 135, 10954.
				Hull, F. J.; Balcells, D.; Sauer, L. O. E.; Raynaud, C.; Brudvig, W. G.; Crabtree, H. R.; Eisenstein, O. J. Am. Chem. Soc. 2010,  132, 7605.
												 doi: 10.1021/ja908744w
											
										
				Sasano, K.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc. 2013, 135, 10954.
												 doi: 10.1021/ja405503y
											
										
 
						
						
						
	                Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
Bowen Xu , Jiahao Chen , Lulu Cui , Xinyue Li , Yuan Xue , Sheng Han . Terpolymers of alkyl methacrylate-trans anethole-1,2,3,6-tetrahydrophthalic anhydride copolymers: A low dosage and high-efficiency cold flow improver for diesel fuel. Chinese Chemical Letters, 2025, 36(5): 110196-. doi: 10.1016/j.cclet.2024.110196
Rong-Nan Yi , Wei-Min He . Electron donor-acceptor complex enabled arylation of dithiocarbamate anions with thianthrenium salts under aqueous micellar conditions. Chinese Chemical Letters, 2024, 35(11): 110194-. doi: 10.1016/j.cclet.2024.110194
Peng Gao , Hua Qiu , Huan Cheng , Zeyu Du , Xiao Chen , Xing Tan , Chenxi Cai , Qihong Zhang , Tong Yang , Nan Lyu , Qiufen Tu , Xingyi Li , Lei Lu , Nan Huang . Robust and versatile surface via in situ dynamic reassembly of polydopamine under strong alkaline conditions. Chinese Chemical Letters, 2025, 36(10): 110746-. doi: 10.1016/j.cclet.2024.110746
Zhen Zhang , Xue-ling Chen , Xiu-Mei Xie , Tian-Yu Gao , Jing Qin , Jun-Jie Li , Chao Feng , Da-Gang Yu . Iron-promoted carbonylation–rearrangement of α-aminoaryl-tethered alkylidenecyclopropanes with CO2: Facile synthesis of quinolinofurans. Chinese Chemical Letters, 2025, 36(4): 110056-. doi: 10.1016/j.cclet.2024.110056
Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
Hui Bian , Xinyi Yuan , Nan Zhang , Zhuo Xu , Juhong Lian , Ruibin Jiang , Junqing Yan , Deng Li , Shengzhong (Frank) Liu . Correlating vacancy-defect density with CO2 activation for promoted CO2 methanation over CsPbBr3 photocatalyst. Chinese Chemical Letters, 2025, 36(7): 111034-. doi: 10.1016/j.cclet.2025.111034
Yang Li , Yanan Dong , Zhihong Wei , Changzeng Yan , Zhen Li , Lin He , Yuehui Li . Fluoride-promoted Ni-catalyzed cyanation of C–O bond using CO2 and NH3. Chinese Chemical Letters, 2025, 36(5): 110206-. doi: 10.1016/j.cclet.2024.110206
Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
Ruonan Yang , Jiajia Li , Dongmei Zhang , Xiuqi Zhang , Xia Li , Han Yu , Zhanhu Guo , Chuanxin Hou , Gang Lian , Feng Dang . Grain-refining Co0.85Se@CNT cathode catalyst with promoted Li2O2 growth kinetics for lithium-oxygen batteries. Chinese Chemical Letters, 2024, 35(12): 109595-. doi: 10.1016/j.cclet.2024.109595
Hai-Yang Song , Jun Jiang , Yu-Hang Song , Min-Hang Zhou , Chao Wu , Xiang Chen , Wei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246
Jinge Zhu , Ailing Tang , Leyi Tang , Peiqing Cong , Chao Li , Qing Guo , Zongtao Wang , Xiaoru Xu , Jiang Wu , Erjun Zhou . Chlorination of benzyl group on the terminal unit of A2-A1-D-A1-A2 type nonfullerene acceptor for high-voltage organic solar cells. Chinese Chemical Letters, 2025, 36(1): 110233-. doi: 10.1016/j.cclet.2024.110233
Yanfen PENG , Xinyue WANG , Tianbao LIU , Xiaoshuo WU , Yujing WEI . Syntheses and luminescence of four Cd(Ⅱ)/Zn(Ⅱ) complexes constructed by 1,3‐bis(4H‐1,2,4‐triazole)benzene. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1416-1426. doi: 10.11862/CJIC.20250018
Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
Jing Cao , Dezheng Zhang , Bianqing Ren , Ping Song , Weilin Xu . Mn incorporated RuO2 nanocrystals as an efficient and stable bifunctional electrocatalyst for oxygen evolution reaction and hydrogen evolution reaction in acid and alkaline. Chinese Chemical Letters, 2024, 35(10): 109863-. doi: 10.1016/j.cclet.2024.109863
Guoxi Yang , Hongji Tan , Jieji Zhu , Qingxiao Tong , Jingxin Jian , Zhihai Yang , Deli Li , Denghui Liu , Shijian Su . [1,2,4]Triazolo[1,5-a]pyridine as regulating unit with high horizontal orientation for efficient non-doped blue OLEDs with negligible efficiency roll-off. Chinese Chemical Letters, 2025, 36(8): 111138-. doi: 10.1016/j.cclet.2025.111138
Qin Cheng , Ming Huang , Qingqing Ye , Bangwei Deng , Fan Dong . Indium-based electrocatalysts for CO2 reduction to C1 products. Chinese Chemical Letters, 2024, 35(6): 109112-. doi: 10.1016/j.cclet.2023.109112