Citation:
Ming-E Wei, Lian-Hui Wang, Yu-Dong Li, Xiu-Ling Cui. Iridium-catalyzed direct ortho-C-H amidation of benzoic acids with sulfonylazides[J]. Chinese Chemical Letters,
;2015, 26(11): 1336-1340.
doi:
10.1016/j.cclet.2015.08.009
-
Amild and efficient iridium-catalyzed ortho-C-H amidation with sulfonyl azides by weakly coordinating carboxylic acid was demonstrated, which provided a novel approach to anthranilic acid derivatives.
-
Keywords:
- Ir-catalysis
-
-
-
[1]
[1] F. Ullmann, Ueber eine neue Darstellungsweise von Phenylathersalicylsaure, Ber. Dtsch. Chem. Ges. 37 (1904) 853-854.
-
[2]
[2] P.E. Fanta, The ullmann synthesis of biaryls, Chem. Rev. 38 (1946) 139-196.
-
[3]
[3] J.F. Hartwig, Evolution of a fourth generation catalyst for the amination and thioetherification of aryl halides, Acc. Chem. Res. 41 (2008) 1534-1544.
-
[4]
[4] D.S. Surry, S.L. Buchwald, Biaryl phosphane ligands in palladium-catalyzed amination, Angew. Chem. Int. Ed. 47 (2008) 6338-6361.
-
[5]
[5] H.Y. Song, D. Chen, C. Pi, X.L. Cui, Y.J. Wu, Palladium(II)-catalyzed direct regioselectively oxidative acylation of azobenzenes with toluene derivatives, J. Org. Chem. 79 (2014) 2955-2962.
-
[6]
[6] Z.Y. Wu, H.Y. Song, X.L. Cui, et al., Sulfonylation of quinoline N-Oxides with aryl sulfonyl chlorides via copper-catalyzed C-H bonds activation, Org. Lett. 15 (2013) 1270-1273.
-
[7]
[7] C.W. Zhu, M.L. Yi, D.H. Wei, et al., Copper-catalyzed direct amination of quinoline N-Oxides via C-H bond activation under mild conditions, Org. Lett. 16 (2014) 1840-1843.
-
[8]
[8] G. Shan, G.Y. Huang, Y. Rao, H. Zhang, Palladium-catalyzed ortho-selective C-H bond chlorination of aromatic ketones, Chin. Chem. Lett. (2015), http://dx.doi.org/ 10.1016/j.cclet.2015.07.011.
-
[9]
[9] T.M. Figg, S. Park, J. Park, S. Chang, Comparative investigations of Cp*-based group 9 metal-catalyzed direct C-H amination of benzamides, Organometallics 33 (2014) 4076-4085.
-
[10]
[10] Q.Z. Zheng, Y.F. Liang, C. Qin, N. Jiao, Ru(II)-catalyzed intermolecular C-H amidation of weakly coordinating ketones, Chem. Commun. 49 (2013) 5654-5656.
-
[11]
[11] J. Kim, S. Chang, Iridium-catalyzed direct C-H amidation with weakly coordinating carbonyl directing groups under mild conditions, Angew. Chem. Int. Ed. 53 (2014) 2203-2207.
-
[12]
[12] J. Kim, J. Kim, S. Chang, Ruthenium-catalyzed direct C-H amidation of arenes including weakly coordinating aromatic ketones, Chem. Eur. J. 19 (2013) 7328-7333.
-
[13]
[13] D. Lee, Y. Kim, S. Chang, Iridium-catalyzed direct arene C-H bond amidation with sulfonyl- and aryl azides, J. Org. Chem. 78 (2013) 11102-11109.
-
[14]
[14] K. Shin, Y. Baek, S. Chang, Direct C-H amination of arenes with alkyl azides under rhodium catalysis, Angew. Chem. Int. Ed. 52 (2013) 8031-8036.
-
[15]
[15] J. Ryu, K. Shin, S.H. Park, J.Y. Kim, S. Chang, Rhodium-catalyzed direct C-H amination of benzamides with aryl azides: a synthetic route to diarylamines, Angew. Chem. Int. Ed. 51 (2012) 9904-9908.
-
[16]
[16] J.Y. Kim, S.H. Park, J. Ryu, et al., Rhodium-catalyzed intermolecular amidation of arenes with sulfonyl azides via chelation-assisted C-H bond activation, J. Am. Chem. Soc. 134 (2012) 9110-9113.
-
[17]
[17] T. Kang, Y. Kim, D. Lee, Z. Wang, S. Chang, Iridium-catalyzed intermolecular amidation of sp3 C-H bonds: late-stage functionalization of an unactivated methyl group, J. Am. Chem. Soc. 136 (2014) 4141-4144.
-
[18]
[18] H. Hwang, J. Kim, J. Jeong, S. Chang, Regioselective introduction of heteroatoms at the C-8 position of quinoline N-Oxides: remote C-H activation using N-Oxide as a stepping stone, J. Am. Chem. Soc. 136 (2014) 10770-10776.
-
[19]
[19] K. Shin, S. Chang, Iridium(III)-catalyzed direct C-7 amination of indolines with organic azides, J. Org. Chem. 79 (2014) 12197-12204.
-
[20]
[20] J. Ryu, K. Shin, S.H. Park, J.Y. Kim, S. Chang, Rhodium-catalyzed direct C-H amination of benzamides with aryl azides: a synthetic route to diarylamines, Angew. Chem. Int. Ed. 124 (2012) 10042-10046.
-
[21]
[21] J. Ryu, J. Kwak, K. Shin, D. Lee, S. Chang, Ir(III)-catalyzed mild C-H amidation of arenes and alkenes: an efficient usage of acyl azides as the nitrogen source, J. Am. Chem. Soc. 135 (2013) 12861-12868.
-
[22]
[22] M. Miura, T. Tsuda, T. Satoh, S. Pivsa-Art, M. Nomura, Oxidative cross-coupling of N-(2'-Phenylphenyl)benzene-sulfonamides or benzoic and naphthoic acids with alkenes using a palladium-copper catalyst system under air, J. Org. Chem. 63 (1998) 5211-5215.
-
[23]
[23] H.A. Chiong, Q.N. Pham, O. Daugulis, Two methods for direct ortho-arylation of benzoic acids, J. Am. Chem. Soc. 129 (2007) 9879-9884.
-
[24]
[24] R. Giri, N. Maugel, J.J. Li, D.H. Wang, S.P. Breazzano, L.B. Saunders, J.Q. Yu, Palladium-catalyzed methylation and arylation of sp2 and sp3 C-H bonds in simple carboxylic acids, J. Am. Chem. Soc. 129 (2007) 3510-3511.
-
[25]
[25] D.H. Wang, T.S. Mei, J.Q. Yu, Versatile Pd(II)-catalyzed C-H activation/aryl- aryl coupling of benzoic and phenyl acetic acids, J. Am. Chem. Soc. 130 (2008) 17676-17677.
-
[26]
[26] T.S. Mei, R. Giri, N. Maugel, J.Q. Yu, Pd(II)-catalyzed monoselective ortho halogenation of C-H bonds assisted by counter cations: a complementary method to directed ortho lithiation, Angew. Chem. Int. Ed. 47 (2008) 5215-5219.
-
[27]
[27] Y.H. Zhang, J.Q. Yu, Pd(II)-catalyzed hydroxylation of arenes with 1 atm of O2 or air, J. Am. Chem. Soc. 131 (2009) 14654-14655.
-
[28]
[28] Y.H. Zhang, B.F. Shi, J.Q. Yu, Palladium(II)-catalyzed ortho alkylation of benzoic acids with alkyl halides, Angew. Chem. Int. Ed. 48 (2009) 6097-6100.
-
[29]
[29] K.M. Engle, D.H. Wang, J.Q. Yu, Constructing multiply substituted arenes using sequential palladium(II)-catalyzed C-H olefination, Angew. Chem. Int. Ed. 49 (2010) 6169-6173.
-
[30]
[30] T.S. Mei, D.H. Wang, J.Q. Yu, Expedient drug synthesis and diversification via ortho-C-H iodination using recyclable PdI2 as the precatalyst, Org. Lett. 14 (2010) 3140-3143.
-
[31]
[31] K.M. Engle, P.S. Thuy-Boun, M. Dang, J.Q. Yu, Ligand-accelerated cross-coupling of C(sp2)-H bonds with arylboron reagents, J. Am. Chem. Soc. 133 (2011) 18183-18193.
-
[32]
[32] D. Lee, S. Chang, Direct C-H amidation of benzoic acids to introduce metaand para-amino groups by tandem decarboxylation, Chem. Eur. J. 21 (2015) 5364-5368.
-
[33]
[33] M.R. Yadav, R.K. Rit, A.K. Sahoo, Sulfoximine directed intermolecular o-C-H amidation of arenes with sulfonyl azides, Org. Lett. 7 (2013) 1638-1641.
-
[34]
[34] S. Doungsoongnuen, A. Worachartcheewan, R. Pingaew, et al., Investigation on biological activities of anthranilic acid sulfonamide analogs, EXCLI J. 10 (2011) 155-161.
-
[1]
-
-
-
[1]
Chaozheng He , Menghui Xi , Chenxu Zhao , Ran Wang , Ling Fu , Jinrong Huo . Highly N2 dissociation catalyst: Ir(100) and Ir(110) surfaces. Chinese Chemical Letters, 2025, 36(3): 109671-. doi: 10.1016/j.cclet.2024.109671
-
[2]
Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
-
[3]
Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
-
[4]
Lin Zhang , Chaoran Li , Thongthai Witoon , Xingda An , Le He . Nano-thermometry in photothermal catalysis. Chinese Journal of Structural Chemistry, 2025, 44(4): 100456-100456. doi: 10.1016/j.cjsc.2024.100456
-
[5]
Yu Mao , Yilin Liu , Xiaochen Wang , Shengyang Ni , Yi Pan , Yi Wang . Acylfluorination of enynes via phosphine and silver catalysis. Chinese Chemical Letters, 2024, 35(8): 109443-. doi: 10.1016/j.cclet.2023.109443
-
[6]
Jiaqi Jia , Kathiravan Murugesan , Chen Zhu , Huifeng Yue , Shao-Chi Lee , Magnus Rueping . Multiphoton photoredox catalysis enables selective hydrodefluorinations. Chinese Chemical Letters, 2025, 36(2): 109866-. doi: 10.1016/j.cclet.2024.109866
-
[7]
Shiqi Peng , Yongfang Rao , Tan Li , Yufei Zhang , Jun-ji Cao , Shuncheng Lee , Yu Huang . Regulating the electronic structure of Ir single atoms by ZrO2 nanoparticles for enhanced catalytic oxidation of formaldehyde at room temperature. Chinese Chemical Letters, 2024, 35(7): 109219-. doi: 10.1016/j.cclet.2023.109219
-
[8]
A-Yang Wang , Sheng-Hua Zhou , Mao-Yin Ran , Xin-Tao Wu , Hua Lin , Qi-Long Zhu . Regulating the key performance parameters for Hg-based IR NLO chalcogenides via bandgap engineering strategy. Chinese Chemical Letters, 2024, 35(10): 109377-. doi: 10.1016/j.cclet.2023.109377
-
[9]
Lilin Song , Mengru Sun , Yuqing Song , Feng Zhang , Bei Zhao , Hairong Zeng , Jinhui Shi , Huixin Liu , Shanshan Zhao , Tian Tian , Heng Yin , Guangbo Ge . Rationally engineered IR-783 octanoate as an enzyme-activatable fluorogenic tool for functional imaging of hNotum in living systems. Chinese Chemical Letters, 2024, 35(11): 109601-. doi: 10.1016/j.cclet.2024.109601
-
[10]
Ning LI , Siyu DU , Xueyi WANG , Hui YANG , Tao ZHOU , Zhimin GUAN , Peng FEI , Hongfang MA , Shang JIANG . Preparation and efficient catalysis for olefins epoxidation of a polyoxovanadate-based hybrid. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 799-808. doi: 10.11862/CJIC.20230372
-
[11]
Uttam Pandurang Patil . Porous carbon catalysis in sustainable synthesis of functional heterocycles: An overview. Chinese Chemical Letters, 2024, 35(8): 109472-. doi: 10.1016/j.cclet.2023.109472
-
[12]
Liliang Chu , Xiaoyan Zhang , Jianing Li , Xuelei Deng , Miao Wu , Ya Cheng , Weiping Zhu , Xuhong Qian , Yunpeng Bai . Continuous-flow synthesis of polysubstituted γ-butyrolactones via enzymatic cascade catalysis. Chinese Chemical Letters, 2024, 35(4): 108896-. doi: 10.1016/j.cclet.2023.108896
-
[13]
Hao-Cong Li , Ming Zhang , Qiyan Lv , Kai Sun , Xiao-Lan Chen , Lingbo Qu , Bing Yu . Homogeneous catalysis and heterogeneous separation: Ionic liquids as recyclable photocatalysts for hydroacylation of olefins. Chinese Chemical Letters, 2025, 36(2): 110579-. doi: 10.1016/j.cclet.2024.110579
-
[14]
Panpan Wang , Hongbao Fang , Mengmeng Wang , Guandong Zhang , Na Xu , Yan Su , Hongke Liu , Zhi Su . A mitochondria targeting Ir(III) complex triggers ferroptosis and autophagy for cancer therapy: A case of aggregation enhanced PDT strategy for metal complexes. Chinese Chemical Letters, 2025, 36(1): 110099-. doi: 10.1016/j.cclet.2024.110099
-
[15]
Ruixue Liu , Xiaobing Ding , Qiwei Lang , Gen-Qiang Chen , Xumu Zhang . Enantioselective and divergent construction of chiral amino alcohols and oxazolidin-2-ones via Ir-f-phamidol-catalyzed dynamic kinetic asymmetric hydrogenation. Chinese Chemical Letters, 2025, 36(3): 110037-. doi: 10.1016/j.cclet.2024.110037
-
[16]
Ruilong Geng , Lingzi Peng , Chang Guo . Dynamic kinetic stereodivergent transformations of propargylic ammonium salts via dual nickel and copper catalysis. Chinese Chemical Letters, 2024, 35(8): 109433-. doi: 10.1016/j.cclet.2023.109433
-
[17]
Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp3)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
-
[18]
Yuhao Guo , Na Li , Tingjiang Yan . Tandem catalysis for photoreduction of CO2 into multi-carbon fuels on atomically thin dual-metal phosphochalcogenides. Chinese Journal of Structural Chemistry, 2024, 43(7): 100320-100320. doi: 10.1016/j.cjsc.2024.100320
-
[19]
Junxin Li , Chao Chen , Yuzhen Dong , Jian Lv , Jun-Mei Peng , Yuan-Ye Jiang , Daoshan Yang . Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis. Chinese Chemical Letters, 2024, 35(11): 109732-. doi: 10.1016/j.cclet.2024.109732
-
[20]
Yingtao Zhong , Ziwen Qiu , Yanmei Li , Jiaqi Huang , Zhenming Lu , Renjiang Kong , Ni Yan , Hong Cheng . Nutrients deprivation of biomimetic nanozymes for cascade catalysis triggered and oxidative damage induced tumor eradication. Chinese Chemical Letters, 2025, 36(3): 109846-. doi: 10.1016/j.cclet.2024.109846
-
[1]
Metrics
- PDF Downloads(0)
- Abstract views(799)
- HTML views(1)