Chinese Journal of Organic Chemistry >
Transition-Metal Free Radical-Mediated C—H Bond Alkynylation and Allylation of Ethers, Aldehydes and Amides
Received date: 2022-07-06
Revised date: 2022-08-14
Online published: 2022-09-02
Supported by
National Natural Science Foundation of China(21971173); National Natural Science Foundation of China(22171201)
Ethers, aldehydes, and amides are widely found in natural products and pharmaceutical molecules, and employed as inexpensive materials in synthetic chemistry. Radical-mediated heteroatomic α-C—H bond functionalization provides an efficient strategy for structural modification of ethers, aldehydes, and amides. New approaches of C—H alkynylation and allylation through phenyliodine bis(trifluoroacetate) (PIFA) induced hydrogen atom transfer (HAT) under visible-light irradiation are reported. The method is operationally simple, leading to the corresponding alkynylated and allylated products in moderate to good yields. The protocol features mild and transition-metal free conditions, broad functional group compatibility, and is adapted to a diversity of ethers, aldehydes, and amides as well as various alkynylating and allylating reagents.
Yaohui Xu , Zhen Wu , Xinxin Wu , Chen Zhu . Transition-Metal Free Radical-Mediated C—H Bond Alkynylation and Allylation of Ethers, Aldehydes and Amides[J]. Chinese Journal of Organic Chemistry, 2022 , 42(12) : 4340 -4349 . DOI: 10.6023/cjoc202207014
| [1] | (a) Kang, E. J.; Lee, E. Chem. Rev. 2005, 105, 4348. |
| [1] | (b) Nakata, T. Chem. Rev. 2005, 105, 4314. |
| [1] | (c) Roughley, S. D.; Jordan, A. M. J. Med. Chem. 2011, 54, 3451. |
| [2] | Wan, M.; Meng, Z.; Lou, H.; Liu, L. Angew. Chem., Int. Ed. 2014, 53, 13845. |
| [3] | (a) Willis, M. C. Chem. Rev. 2010, 110, 725. |
| [3] | (b) Chinchilla, R.; Najera, C. Chem. Rev. 2014, 114, 1783. |
| [4] | Mukherjee, S.; Garza-Sanchez, R. A.; Tlahuext-Aca, A.; Glorius, F. Angew. Chem., Int. Ed. 2017, 56, 14723. |
| [5] | Gong, J.; Fuchs, P. L. J. Am. Chem. Soc. 1996, 118, 4486. |
| [6] | Hoshikawa, T.; Kamijo, S.; Inoue, M. Org. Biomol. Chem. 2013, 11, 164. |
| [7] | Zhang, R.-Y.; Xi, L.-Y.; Zhang, L.; Liang, S.; Chen, S.-Y.; Yu, X.-Q. RSC Adv. 2014, 4, 54349. |
| [8] | Paul, S.; Guin, J. Green Chem. 2017, 19, 2530. |
| [9] | (a) Praveen Rao, P. N.; Jashim Uddin, M. D.; Knaus, E. E. J. Med. Chem. 2004, 47, 3972. |
| [9] | (b) Arai, T.; Ikematsu, Y.; Suemitsu, Y. Pure Appl. Chem. 2010, 82, 1485. |
| [9] | (c) Fraile, A.; Parra, A.; Tortosa, M.; Alemán, J. Tetrahedron 2014, 70, 9145. |
| [9] | (d) Abbiati, G.; Arcadi, A.; Marinelli, F.; Rossi, E. Synthesis 2014, 46, 687. |
| [10] | (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467. |
| [10] | (b) Chinchilla, R.; Nájera, C. Chem. Rev. 2007, 107, 874. |
| [10] | (c) Chinchilla, R.; Nájera, C. Chem. Soc. Rev. 2011, 40, 5084. |
| [10] | (d) Dudnik, A.; Gevorgyan, V. Angew. Chem., Int. Ed. 2010, 49, 2096. |
| [11] | (a) Brown, H. C.; Garg, C. P. J. Am. Chem. Soc. 1961, 83, 2952. |
| [11] | (b) Jackson, M. M.; Leverett, C.; Toczko, J. F.; Roberts, J. C. J. Org. Chem. 2002, 67, 5032. |
| [11] | (c) Maeda, Y.; Kakiuchi, N.; Matsumura, S.; Nishimura, T.; Kawamura, T.; Uemura, S. J. Org. Chem. 2002, 67, 6718. |
| [11] | (d) Annabelle, L. K.; Shi Shun, E. T.; Chernick, S. E.; Tykwinski, R. R. J. Org. Chem. 2003, 68, 1339. |
| [11] | (e) Augé, J.; LubinGermain, N.; Seghrouchni, L. Tetrahedron Lett. 2003, 41, 819. |
| [11] | (f) Ushijima, S.; Dohi, S.; Moriyama, K.; Togo, H. Tetrahedron 2012, 68, 1436. |
| [11] | (g) Harigae, R.; Moriyama, K.; Togo, H. J. Org. Chem. 2014, 79, 2049. |
| [11] | (h) Yuan, J.; Wang, J.; Zhang, G.; Liu, C.; Qi, X.; Lan, Y.; Miller, J. T.; Kropf, A. J.; Bunel, E. E.; Lei, A. Chem. Commun. 2015, 51, 576. |
| [12] | (a) Kakusawa, N.; Yamaguchi, K.; Kurita, J.; Tsuchiya, T. Tetrahedron Lett. 2000, 41, 4143. |
| [12] | (b) Karpov, A. S.; Müller, T. J. J. Org. Lett. 2003, 5, 3451. |
| [12] | (c) Chen, L.; Li, C.-J. Org. Lett. 2004, 6, 3151. |
| [12] | (d) Alonso, D. A.; Nájera, C.; Pacheco, M. C. J. Org. Chem. 2004, 69, 1615. |
| [12] | (e) Wang, B.; Bonin, M.; Micouin, L. J. Org. Chem. 2005, 70, 6126. |
| [12] | (f) D’Souza, D. M.; Müller, T. J. J. Nat. Protoc. 2008, 3, 1660. |
| [12] | (g) Sun, W.; Wang, Y.; Wu, X.; Yao, X. Green Chem. 2013, 15, 2356. |
| [12] | (h) Taylor, C.; Bolshan, Y. Org. Lett. 2014, 16, 488. |
| [12] | (i) Yin, W.; He, H.; Zhang, Y.; Luo, D.; He, H. Synthesis 2014, 46, 2617. |
| [13] | (a) Kobayashi, T.; Tanaka, M. J. Chem. Soc., Chem. Commun. 1981, 7, 333. |
| [13] | (b) Beller, M.; Cornils, B.; Frohning, C. D.; Kohlpaintner, C. W. J. Mol. Catal. A: Chem. 1995, 104, 17. |
| [13] | (c) Mohamed Ahmed, M. S.; Mori, A. Org. Lett. 2003, 5, 3057. |
| [13] | (d) Karpov, A. S.; Merkul, E.; Rominger, F.; Müller, T. J. J. Angew. Chem., Int. Ed. 2005, 44, 6951. |
| [13] | (e) Liang, B.; Huang, M.; You, Z.; Xiong, Z.; Lu, K.; Fathi, R.; Chen, J.; Yang, Z. J. Org. Chem. 2005, 70, 6097. |
| [13] | (f) Liu, J.; Chen, J.; Xia, C. J. Catal. 2008, 253, 50. |
| [13] | (g) Fusano, A.; Fukuyama, T.; Nishitani, S.; Inouye, T.; Ryu, I. Org. Lett. 2010, 12, 2410. |
| [13] | (h) Genelot, M.; Dufaud, V.; Djakovitch, L. Adv. Synth. Catal. 2013, 355, 2604. |
| [13] | (i) Brennführer, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 4114. |
| [14] | Ouyang, X.-H.; Song, R.-J.; Wang, C.-Y.; Yang, Y.; Li, J.-H. Chem. Commun. 2015, 51, 14497. |
| [15] | Wang, H.; Guo, L.-N.; Wang, S.; Duan, X.-H. Org. Lett. 2015, 17, 3054. |
| [16] | Mukherjee, S.; Garza-Sanchez, R. A.; Tlahuext-Aca, A.; Glorius, F. Angew. Chem., Int. Ed. 2017, 56, 14723. |
| [17] | Li, L.; Guo, S.; Wang, Q.; Zhu, J. Org. Lett. 2019, 21, 5462. |
| [18] | (a) Wu, X.; Zhang, H.; Tang, N.; Wu, Z.; Wang, D.; Ji, M.; Xu, Y.; Wang, M.; Zhu, C. Nat. Commun. 2018, 9, 3343. |
| [18] | (b) Tang, N.; Wu, X.; Zhu, C. Chem. Sci. 2019, 10, 6915. |
| [18] | (c) Shao, X.; Wu, X.; Wu, S.; Zhu, C. Org. Lett. 2020, 22, 7450. |
| [19] | Wang, X.; Shao, X.; Cao, Z.; Wu, X.; Zhu, C. Adv. Synth. Catal. 2022, 364, 1200. |
| [20] | Li, X.; Liu, C.; Guo, S.; Wang, W.; Zhang, Y. Eur. J. Org. Chem. 2021, 3, 411. |
/
| 〈 |
|
〉 |
