Abstract
A new route to bidentate amide directing groups has been developed via the palladium(II)-catalyzed aminocarbonylation. Under atmospheric carbon monoxide pressure, using commercially available aryl iodides and aromatic amine derivatives as substrates, the three-component reaction proceeded smoothly to give the desired products in moderate-to-excellent yields with good functional-group compatibility.
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Notes
For selected reviews on transition metals catalyzed C–H functionalization.
References
Ma W, Kaplaneris N, Fang X, Gu L, Mei R, Ackermann L (2020) Org Chem Front 7:1022
Borpatra PJ, Deka B, Deb ML, Baruah PK (2019) Org Chem Front 6:3445
Dey A, Thrimurtulu N, Volla CMR (2019) Org Lett 21:3871
Rao W-H, Shi B-F (2016) Org Chem Front 3:1028
Chen Z, Wang B, Zhang J, Yu W, Liu Z, Zhang Y (2015) Org Chem Front 2:1107
Yang L, Huang H (2015) Chem Rev 115:3468
Gao K, Yoshikai N (2014) Acc Chem Res 47:1208
Wencel-Delord J, Droge T, Liu F, Glorius F (2011) Chem Soc Rev 40:4740
Giri R, Shi BF, Engle KM, Maugel N, Yu JQ (2009) Chem Soc Rev 38:3242
Guo X-K, Zhang L-B, Wei D, Niu J-L (2015) Chem Sci 6:7059
Zaitsev VG, Shabashov D, Daugulis O (2005) J Am Chem Soc 127:13154
Li Q, Huang J, Chen G, Wang S-B (2020) Org Biomol Chem 18:4802
Liu X, Zhang H, Yang F (2019) Bo Wang. Org Biomol Chem 17:7564
Ueno R, Natsui S, Chatani N (2018) Org Lett 20:1062
Kommagalla Y, Yamazaki K, Yamaguchi T, Chatani N (2018) Chem Commun 54:1359
Zhu L, Cao X, Li Y, Liu T, Wang X, Qiu R, Yin S-F (2017) Chin J Org Chem 37:1613
Vinayak B, NavyaSree P, Chandrasekharam M (2017) Org Biomol Chem 15:9200
Lin C, Chen Z, Liu Z, Zhang Y (2017) Org Lett 19:850
Iwasaki M, Miki N, Tsuchiya Y, Nakajima K, Nishihara Y (2017) Org Lett 19:1092
Sun S-Z, Shang M, Xu H, Cheng T-J, Li M-H, Dai H-X (2020) Chem Commun 56:1444
Hu F-P, Cui X-F, Lu G-Q, Huang G-S (2020) Org Biomol Chem 18:4376
Gao T-H, Wang C-M, Tang K-X, Xu Y-G, Sun L-P (2019) Eur J Org Chem 19:3005
Wan L, Qiao K, Yuan X, Zheng M-W, Fan B-B, Di ZC, Zhang D, Fang Z, Guo K (2017) Adv Synth Catal 359:2596
Liu J, Xue Z, Zeng Z, Chen Y, Chen G (2016) Adv Synth Catal 358:3694
Wang H-L, Shang M, Sun S-Z, Zhou Z-L, Laforteza BN, Dai H-X, Yu J-Q (2015) Org Lett 17:1228
Shang M, Sun S-Z, Dai H-X, Yu J-Q (2014) J Am Chem Soc 136:3354
Shang M, Wang H-L, Sun S-Z, Dai H-X, Yu J-Q (2014) J Am Chem Soc 136:11590
Ding Y, Han Y-Q, Wu L-S, Zhou T, Yao Q-J, Feng Y-L, Li Y, Kong K-X, Shi B-F (2020) Angew Chem Int Ed. https://doi.org/10.1002/anie.202004504
Zhou T, Jiang M-X, Yang X, Yue Q, Han Y-Q, Ding Y, Shi B-F (2020) Chin J Chem 38:242
Han Y-Q, Ding Y, Zhou T, Yan S-Y, Song H, Shi B-F (2019) J Am Chem Soc 141:4558
Yan S-Y, Han Y-Q, Yao Q-J, Nie X-L, Liu L, Shi B-F (2018) Angew Chem Int Ed 57:9093
Li Y, Liu Y-J, Shi B-F (2017) Adv Synth Catal 359:4117
Chen F-J, Zhao S, Hu F, Chen K, Zhang Q, Zhang S-Q, Shi B-F (2013) Chem Sci 4:4187
Fan C-L, Zhang L-B, Liu J, Hao X-Q, Niu J-L, Song M-P (2019) Org Chem Front 6:2215
Du C, Li P-X, Zhu X, Suo J-F, Niu J-L, Song M-P (2016) Angew Chem Int Ed 55:13571
Zhang L-B, Hao X-Q, Liu Z-J, Zheng X-X, Zhang S-K, Niu J-L, Song M-P (2015) Angew Chem Int Ed 54:10012
Hao X-Q, Chen L-J, Ren B, Li L-Y, Yang X-Y, Gong J-F, Niu J-L, Song M-P (2014) Org Lett 16:1104
Shen Y, Cindy Lee W-C, Gutierrez DA, Li JJ (2017) J Org Chem 82:11620
Mane RS, Bhanage BM (2017) Adv Synth Catal 359:2621
Gergely M, Boros B, Kollar L (2017) Tetrahedron 73:6736
Liu S, Deng Q, Fang W, Gong J-F, Song M-P, Xu M, Tu T (2014) Org Chem Front 1:1261
Wang T, Wang R, Wang W, Zhang A, Liu L (2018) J Organomet Chem 858:62
Mukherjee A, Subramanyam U, Puranik VG, Mohandas TP, Sarkar A (2005) Eur J Inorg Chem 1254
Korshin EE, Sabirova LA, Levin YA (2012) Synthesis 44:3512
Ouyang K, Xi Z (2013) Acta Chim Sin 71:13
Acknowledgements
We are grateful to the Key Science Research of Education Committee in Henan Province (19A150035), the Key Scientific and Technological Project of Henan Province (192102110222), the Program for Science & Technology Innovation Talents in Universities of Henan Province (14HASTIT016) and the Program of Science and Technology Innovation Talents of Henan Province (No. 2018JQ0011).
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Wang, Y., Wang, T., Wang, X. et al. Palladium-catalyzed aminocarbonylation of aryl iodides with amines: efficient access to bidentate amide directing groups. Transit Met Chem 46, 29–35 (2021). https://doi.org/10.1007/s11243-020-00418-4
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DOI: https://doi.org/10.1007/s11243-020-00418-4