Recent Advance of Acyclic Diaryliodonium Salts in Arylation of Heteroatom
- Corresponding author: Cheng Huicheng, awchengcheng@163.com
	            Citation:
	            
		            Ma Jiaoli, Chen Licheng, Yuan Zhongwen, Cheng Huicheng. Recent Advance of Acyclic Diaryliodonium Salts in Arylation of Heteroatom[J]. Chinese Journal of Organic Chemistry,
							;2018, 38(7): 1586-1595.
						
							doi:
								10.6023/cjoc201802021
						
					
				
					 
				
	        
 
	                
				(a) Zhdankin, V. V. Hypervalent Iodine Chemistry: Preparation, Structure, and Synthetic Applications of Polyvalent Iodine Compounds, Wiley, Chichester, 2013. 
(b) Wirth, T. Hypervalent Iodine Chemistry, Springer, Berlin, 2003. 
(c) Varvoglis, A. Hypervalent Iodine in Organic Syntheses, Academic Press, San Diego, 1996. 
(d) Zhdankin, V. V. ARKIVOC 2009, (i), 1. 
(e) Wirth, T. Angew. Chem. Int. Ed. 2005, 117, 3722. 
(f) Richardson, R. D. ; Wirth, T. Angew. Chem., Int. Ed. 2006, 45, 4402. 
(g) Zhang, X. ; Cong, Y. ; Lin, G. -Y. ; Guo, X. -L. ; Cao, Y. ; Lei, K. -H. ; Du, Y. -F. J. Org. Chem. 2016, 36, 2513 (in Chinese). 
(张翔, 丛颖, 林光宇, 郭旭亮, 曹阳, 雷坤华, 杜云飞, 有机化学, 2016, 36, 2513.) 
(h) Duan, Y. -N. ; Jiang, S. ; Han, Y. -C. ; Sun, B. ; Zhang, C. J. Org. Chem. 2016, 36, 973 (in Chinese). 
(段亚南, 姜山, 韩永超, 孙博, 张弛, 有机化学, 2016, 36, 1973.)
				(a) Koser, G. F. ; Wettach, R. H. ; Smith, C. S. J. Org. Chem. 1980, 45, 1543. 
(b) Stang, P. J. ; Zhdankin, V. V. ; Tykwinski, R. Tetrahedron Lett. 1992, 33, 1419. 
(c) Merritt, E. A. ; Olofsson, B. Angew. Chem. Int. Ed. 2009, 48, 9052. 
(d) Bielawski, M. ; Olofsson, B. Chem. Commun. 2007, 25, 2521. 
(e) Bielawski, M. ; Zhu, M. ; Olofsson, B. Adv. Synth. Catal. 2007, 349, 2610. 
(f) Bielawski, M. ; Olofsson, B. Chem. Commun. 2007, 2521. 
(g) Zhu, M. ; Jalalian, N. ; Olofsson, B. Synlett 2008, 592. 
(h) Yusubov, M. S. ; Maskaev, A. V. ; Zhdankin, V. V. ARKIVOC 2011, (i), 370. 
(i) Xiao, Z. -C. ; Xia, C. -F. Chin. J. Org. Chem. 2013, 33, 2119 (in Chinese). 
(肖志超, 夏成峰, 有机化学, 2013, 33, 2119.) 
(j) Zhang, B. -X. ; Zhao, X. -Y. ; Wu, Q. ; Guo, Y. -L. Prog. Chem. 2013, 25, 1142 (in Chinese). 
(张变香, 赵晓芸, 吴群, 郭一力, 化学进展, 2013, 25, 1142.) 
(k) Olofsson, B. Top. Curr. Chem. 2015, 373, 135. (l) Aradi, K. ; Tóth, B. L. ; Tolnai, G. L. ; Novák, Z. Synlett 2016, 27, 1456.
				Hartmann, C.; Meyer, V. Ber. Dtsch. Chem. Ges. 1894, 27, 426.
												 doi: 10.1002/(ISSN)1099-0682
											
										
				(a) Koser, G. F. ; Wettach, R. H. ; Smith, C. S. J. Org. Chem. 1980, 45, 1543. 
(b) Carman C. S. ; Koser G. F. J. Org. Chem. 1983, 48, 2534. 
(c) Margida A. J. ; Koser G. F. J. Org. Chem. 1984, 49, 3643. 
(d) Kitamura T. ; Matsuyuki J. ; Taniguchi H. Synthesis 1994, 147. 
(e) Mascarelli, L. ; Benati. G. Gazz. Chim Ital. 1908, 38, 627. 
(f) Merritt, E. A. ; Malmgren, J. ; Klinke, F. J. ; Olofsson, B. Synlett 2009, 2277. 
(g) Bielawski, M. ; Aili, D. ; Olofsson, B. J. Org. Chem. 2008, 73, 4602. 
(h) Lindstedt, E. ; Reitti, M. ; Olofsson, B. J. Org. Chem. 2017, 82, 11909. 
(i) Grushin, V. V. Chem. Soc. Rev. 2000, 29, 315. 
(j) Chatterjee, N. ; Goswami, A. Eur. J. Org. Chem. 2017, 3023.
				(a) Stang P. J. ; Zhdankin V. V. Chem. Rev. 1996, 96, 1123. 
(b) Olofsson B. ; Merritt. E. A. Angew. Chem., Int. Ed. 2009, 48, 9052.
				(a) Der Puy, M. V. J. Fluorine Chem. 1982, 21, 385. 
(b) Pike, V. W. ; Aigbirhio, F. I. J. Chem. Soc., Chem. Commun. 1995, 2215. 
(c)Shah, A. ; W. Pike, V. ; A. Widdowson, D. J. Chem. Soc., Perkin Trans. 1 1998, (13), 2043. 
(d) Graskemper, J. W. ; Wang, B. ; Qin, L. ; Neumann, K. D. ; DiMagno, S. G. Org. Lett. 2011, 13, 3158.
				(a) Ichiishi, N. ; Canty, A. J. ; Yates, B. F. ; Sanford, M. S. Org. Lett. 2013, 15, 5134. 
(b)Ichiishi, N. ; Canty, A. J. ; Yates, B. F. ; Sanford, M. S. Organometallics 2014, 33, 5525. 
(c) Ichiishi, N. ; Brooks, A. F. ; Topczewski, J. J. ; Rodnick, M. E. ; Sanford, M. S. ; Scott, P. J. H. Org. Lett. 2014, 16, 3224.
				Moon, B. S.; Kil, H. S.; Park, J. H.; Kim, J. S.; Park, J.; Chi, D. Y.; Lee, B. C.; Kim, S. E. Org. Biomol. Chem. 2011, 9, 8346.
												 doi: 10.1039/c1ob06277h
											
										
				Chun, J.-H.; Pike, V. W. Org. Biomol. Chem. 2013, 11, 6300.
												 doi: 10.1039/c3ob41353e
											
										
				(a) Rotstein, B. H. ; Stephenson, N. A. ; Vasdev, N. ; Liang, S. H. Nat. Commun. 2014, 5, 4365. 
(b) Calderwood, S. ; Collier, T. L. ; Gouverneur, V. ; Liang, S. H. ; Vasdev, N. J. Fluorine Chem. 2015, 178, 249.
				Carrol, M. A.; Wood, R. A. Tetrahedron 2007, 63, 11349.
												 doi: 10.1016/j.tet.2007.08.076
											
										
				Sandtorv, A. H.; Stuart, D. R. Angew. Chem., Int. Ed. 2016, 55, 15812.
												 doi: 10.1002/anie.201610086
											
										
				Yang, Y.; Wu, X.; Han, J.; Mao, S.; Qian, X.; Wang, L. Eur. J. Org. Chem. 2014, 6854.
										
				Riedmüller, S.; Nachtsheim, B. J. Synlett 2015, 26, 651.
												 doi: 10.1055/s-00000083
											
										
				Pang, X.; Lou, Z.; Li, M.; Wen, L.; Chen, C. Eur. J. Org. Chem. 2015, 3361.
										
				Geng, X.; Mao, S.; Chen, L.; Yu, J.; Han, J.; Hua, J.; Wang, L. Tetrahedron Lett. 2014, 55, 3856.
												 doi: 10.1016/j.tetlet.2014.05.082
											
										
				Tinnis, F.; Stridfeldt, E.; Lundberg, H.; Adolfsson, H.; Olofsson, B. Org. Lett. 2015, 17, 2688.
												 doi: 10.1021/acs.orglett.5b01079
											
										
				Lucchetti, N.; Scalone, M.; Fantasia, S.; Muiz, K. Angew. Chem., Int. Ed. 2016, 55, 13335.
												 doi: 10.1002/anie.201606599
											
										
				Yang, Q.; He, X.-X.; Chang, J.; Wu, Q.; Zhang, B.-X. Chin. J. Org. Chem. 2011, 31, 1687 (in Chinese).
										 
				Guo, F.; Wang, L.; Wang, P.; Yu, J.; Han, J. Asian J. Org. Chem. 2012, 1, 218.
												 doi: 10.1002/ajoc.v1.3
											
										
				Gonda, Zs.; Novák, Z. Chem. Eur. J. 2015, 21, 16801.
												 doi: 10.1002/chem.v21.47
											
										
				Modha, S. G.; Greaney, M. F. J. Am. Chem. Soc. 2015, 137, 1416.
												 doi: 10.1021/ja5124754
											
										
				Reitti, M.; Villo, P.; Olofsson, B. Angew. Chem. Int. Ed. 2016, 55, 8928.
												 doi: 10.1002/anie.201603175
											
										
				Li, X.; Li, L.; Mo, X.; Mo, D. Synth. Commun. 2016, 46, 963.
												 doi: 10.1080/00397911.2016.1181764
											
										
				Wang, Y.; Chen, C.; Peng, J.; Li, M. Angew. Chem., Int. Ed. 2013, 52, 5323.
												 doi: 10.1002/anie.201300586
											
										
				Su, X.; Chen, C.; Wang, Y.; Chen, J.; Lou, Z.; Li, M. Chem. Commun. 2013, 49, 6752.
												 doi: 10.1039/c3cc43216e
											
										
				(a) Cahard, E. ; Bremeyer, N. ; Gaunt, M. J. Angew. Chem., Int. Ed. 2013, 52, 9284. 
(b) Sinai, Á. ; Mészáros, Á. ; Gáti, T. ; Kudar, V. ; Pallò, A. ; Novák, Z. Org. Lett. 2013, 15, 5654. 
(c) Wang, Y. ; Chen, C. ; Peng, J. ; Li, M. Angew. Chem., Int. Ed. 2013, 52, 5323. 
(d) Zhang, F. ; Das, S. ; Walkinshaw, A. J. ; Casitas, A. ; Taylor, M. ; Suero, M. G. ; Gaunt, M. J. J. Am. Chem. Soc. 2014, 136, 8851.
				(a) Aradi, K. ; Bombicz, P. ; Novák, Z. J. Org. Chem. 2016, 81, 920. 
(b) Wen, R. -L. ; Dou, Q. ; Wang, Y. -C. ; Zhang, J. -W. ; Guo, W. -S. ; Li, M. J. Org. Chem. 2017, 82, 1428. 
(c) Wen, R. -L. ; Shen, Q. -Y. ; Guo, W. -S. ; Li, M. Org. Chem. Front. 2016, 3, 870. 
(d) Chi, Y. ; Yan, H. ; Zhang, W. -X. ; Xi, Z. Org. Lett. 2017, 19, 2694.
				(a) Chi, Y. ; Yan, H. ; Zhang, W. -X. ; Xi, Z. Org. Lett. 2017, 19, 2694. 
(b) Oh, K. H. ; Kim, J. G. ; Park, J. K. Org. Lett. 2017, 19, 3994.
				Li, P.; Cheng, G.; Zhang, H.; Xu, X.; Gao, J.; Cui, X. J. Org. Chem. 2014, 79, 8156.
												 doi: 10.1021/jo501334u
											
										
				Xiang, S.-K.; Li, J.-M.; Huang, H.; Feng, C.; Ni, H.-L.; Chen, X.-Z.; Wang, B.-Q.; Zhao, K.-Q.; Hu, P.; Redshaw, C. Adv. Synth. Catal. 2015, 357, 3435.
												 doi: 10.1002/adsc.201500651
											
										
				(a) Beringer, F. M. ; Gindler, E. M. J. Am. Chem. Soc. 1955, 77, 3203. 
(b) Caserio, M. C. ; Glusker, D. L. ; Roberts, J. D. J. Am. Chem. Soc. 1959, 81, 336.
				(a) Jalalian, N. ; Ishikawa, E. E. ; Silva, L. F. Jr. ; Olofson, B. Org. Lett. 2011, 13, 1552. 
(b) Jalalian, N. ; Petersen, T. B. ; Olofsson, B. Chem. Eur. J. 2012, 18, 14140. 
(c) Lindstedt, E. ; Ghosh, R. ; Olofsson, B. Org. Lett. 2013, 15, 6070. 
(d) Chan, L. ; McNally, A. ; Toh, Q. Y. ; Mendoza, A. ; Gaunt, M. J. Chem. Sci. 2015, 6, 1277.
				Thorat, P. B.; Waghmode, N. A.; Karade, N. N. Tetrahedron Lett. 2014, 55, 5718.
												 doi: 10.1016/j.tetlet.2014.08.079
											
										
				(a) Lubinovski, J. J. ; Knapczyk, J. W. ; Calderon, J. L. ; Petit, L. R. ; McEwen, W. E. J. Org. Chem. 1975, 40, 3010. 
(b) Ghosh, R. ; Lindstedt, E. ; Jalalian, N. ; Olofsson, B. ChemistryOpen 2014, 3, 54.
				Sundalam, S. K.; Stuart, D. R. J. Org. Chem. 2015, 80, 6456.
												 doi: 10.1021/acs.joc.5b00907
											
										
				Tolnai, G. L.; Nilsson, U. J.; Olofsson, B. Angew. Chem., Int. Ed. 2016, 55, 11226.
												 doi: 10.1002/anie.201605999
											
										
				Kumar, D.; Arun, V.; Pilania, M.; Shekar, K. P. C. Synlett 2013, 24, 831.
												 doi: 10.1055/s-00000083
											
										
				Xiong, B.; Feng, X.; Zhu, L.; Chen, T.; Zhou, Y.; Au, C.-T.; Yin, S.-F. ACS Catal. 2015, 5, 537.
												 doi: 10.1021/cs501523g
											
										
				Bhattarai, B.; Tay, J.-H.; Nagorny, P. Chem. Commun. 2015, 51, 5398.
												 doi: 10.1039/C4CC08604J
											
										
				Sandin, R. B.; Christiansen, R. G.; Brown, R. K.; Kirkwood, S. J. Am. Chem. Soc. 1947, 69, 1550.
										 
				Huang, X.; Zhu, Q.; Xu, Y. Synth. Commun. 2001, 31, 2823.
												 doi: 10.1081/SCC-100105332
											
										
				Wagner, A. M.; Sanford, M. S. J. Org. Chem. 2014, 79, 2263.
												 doi: 10.1021/jo402567b
											
										
				Cullen, S. C.; Shekhar, S.; Nere, N. K. J. Org. Chem. 2013, 78, 12194.
												 doi: 10.1021/jo401868x
											
										
				Saravanan, P.; Anbarasan, P. Adv. Synth. Catal. 2015, 357, 3521.
												 doi: 10.1002/adsc.201500606
											
										
				Nikolaienko, P.; Yildiz, T.; Rueping, M. Eur. J. Org. Chem. 2016, 1091.
										 
				Xu, J.; Zhang, P. B.; Gao, Y.; Chen, Y.; Tang, G.; Zhao, Y. J. Org. Chem. 2013, 78, 8176.
												 doi: 10.1021/jo4012199
											
										
				Miralles, N.; Romero, R. M.; Fernandez, E.; Muniz, K. Chem. Commun. 2015, 51, 14068.
												 doi: 10.1039/C5CC04944J
											
										
 
						
						
						
	                Nan Xiao , Fang Sun . 二芳基硫醚化合物的构建及应用. University Chemistry, 2025, 40(6): 360-363. doi: 10.12461/PKU.DXHX202407099
Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
Wei HE , Jing XI , Tianpei HE , Na CHEN , Quan YUAN . Application of solar-driven inorganic semiconductor-microbe hybrids in carbon dioxide fixation and biomanufacturing. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 35-44. doi: 10.11862/CJIC.20240364
Shiyang He , Dandan Chu , Zhixin Pang , Yuhang Du , Jiayi Wang , Yuhong Chen , Yumeng Su , Jianhua Qin , Xiangrong Pan , Zhan Zhou , Jingguo Li , Lufang Ma , Chaoliang Tan . Pt Single-Atom-Functionalized 2D Al-TCPP MOF Nanosheets for Enhanced Photodynamic Antimicrobial Therapy. Acta Physico-Chimica Sinica, 2025, 41(5): 100046-0. doi: 10.1016/j.actphy.2025.100046
Zhiwen HUANG , Qi LIU , Jianping LANG . W/Cu/S cluster-based supramolecular macrocycles and their third-order nonlinear optical responses. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 79-87. doi: 10.11862/CJIC.20240184
Jiageng Li , Putrama . 数值积分耦合非线性最小二乘法一步确定反应动力学参数. University Chemistry, 2025, 40(6): 364-370. doi: 10.12461/PKU.DXHX202407098
Zhongyan Cao , Shengnan Jin , Yuxia Wang , Yiyi Chen , Xianqiang Kong , Yuanqing Xu . Advances in Highly Selective Reactions Involving Phenol Derivatives as Aryl Radical Precursors. University Chemistry, 2025, 40(4): 245-252. doi: 10.12461/PKU.DXHX202405186
Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
Yujie WANG , Laobang WANG , Zheng ZHANG , Qi LIU , Jianping LANG . Construction of W/Cu/S cluster-based supramolecular compounds via alkynyl/sulfur cycloaddition and their third-order nonlinear optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2069-2077. doi: 10.11862/CJIC.20250129
Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
Min LIU , Huapeng RUAN , Zhongtao FENG , Xue DONG , Haiyan CUI , Xinping WANG . Neutral boron-containing radical dimers. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 123-130. doi: 10.11862/CJIC.20240362
Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
Xinghai Liu , Hongke Wu . Exploration and Practice of Ideological and Political Education in Heterocyclic Chemistry Based on "Fentanyl" Event. University Chemistry, 2024, 39(8): 359-364. doi: 10.3866/PKU.DXHX202312100
Mengyang LI , Hao XU , Zhonghao NIU , Chunhua GONG , Weihui ZHONG , Jingli XIE . Highly effective catalytic synthesis of β-amino alcohols by using viologen-polyoxometalate hybrid materials. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1294-1300. doi: 10.11862/CJIC.20250080
Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
Guoxian Zhu , Jing Chen , Rongkai Pan . Enhancing the Teaching Quality of Atomic Structure: Insights and Strategies. University Chemistry, 2024, 39(3): 376-383. doi: 10.3866/PKU.DXHX202305027
Jin Jia , Shangda Jiang . Is the z Axis Special in Atomic Structure?. University Chemistry, 2024, 39(6): 400-404. doi: 10.12461/PKU.DXHX202403091
Linhan Tian , Changsheng Lu . Discussion on Sextuple Bonding in Diatomic Motifs of Chromium Family Elements. University Chemistry, 2024, 39(8): 395-402. doi: 10.3866/PKU.DXHX202401056
Tingting XU , Wenjing ZHANG , Yongbo SONG . Research advances of atomic precision coinage metal nanoclusters in tumor therapy. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2275-2285. doi: 10.11862/CJIC.20240229
Lele Feng , Xueying Bai , Jifeng Pang , Hongchen Cao , Xiaoyan Liu , Wenhao Luo , Xiaofeng Yang , Pengfei Wu , Mingyuan Zheng . Single-atom Pd boosted Cu catalysts for ethanol dehydrogenation. Acta Physico-Chimica Sinica, 2025, 41(9): 100100-0. doi: 10.1016/j.actphy.2025.100100