Citation: Jianxia Chen, Chaolumen Bai, Hongpeng Ma, Dan Liu, Yong-Sheng Bao. Nano palladium catalyzed C(sp³)—H bonds arylation by a transient directing strategy[J]. Chinese Chemical Letters, ;2021, 32(1): 465-469. doi: 10.1016/j.cclet.2020.02.055 shu

Nano palladium catalyzed C(sp³)—H bonds arylation by a transient directing strategy

College of Chemistry and Environmental Science, Inner Mongolia Key Laboratory of Green Catalysis, Inner Mongolia Normal University, Hohhot 010022, China

sbbys197812@163.com

Received Date: 9 January 2020
Revised Date: 16 February 2020
Accepted Date: 28 February 2020
Available Online: 29 February 2020

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Reported herein is the first example of heterogeneous palladium catalyzed C(sp³)-H bonds arylation by a transient-ligand-directed strategy. Using supported palladium (metallic state) nanopariticles as catalyst, a wide range of aryl iodides undergo the coupling with various o-methylbenzaldehyde derivatives to assemble a library of highly selective and functionalized o-benzylbenzaldehydes. The stability of the catalyst was easily recovered four runs without significant loss of activity. The XPS analysis of the catalyst before and after reaction indicated that the reaction might be carried out by a catalytic cycle starting with Pd⁰.
- C(sp³)-H functionalization,
- Transient directing group,
- Palladium,
- Nanoparticles catalyst,
- Arylation
1. [1]
  (a) N. Selander, K.J. Szabo', Chem. Rev. 111 (2011) 2048-2076;
  (b) V.G. Zaitsev, D. Shabashov, O. Daugulis, J. Am. Chem. Soc.127 (2005) 13154-13155;
  (c) A. Roglans, A. Pla-Quintana, M. Moreno-Maňas, Chem. Rev. 106 (2006) 4622-4643;
  (d) H.A. Chiong, Q.N. Pham, O. Daugulis, J. Am. Chem. Soc. 129 (2007) 9879-9884;
  (e) K.L. Hull, M.S. Sanford, J. Am. Chem. Soc. 131 (2009) 9651-9653;
  (f)D. Kalyani, N.R. Deprez, L.V. Desai, M.S. Sanford, J. Am. Chem. Soc.127 (2005) 7330-7331;
  (g) J. Park, M. Kim, S. Sharma, et al., Chem. Commun. 49 (2013) 1654-1656;
  (h)Y.Gao, Y.B.Huang, W.Q. Wu, K.Huang, H.F.Jiang, Chem. Commun. 50 (2014) 8370-8373.
2. [2]
  (a) Z. Huang, H.N. Lim, F. Mo, M.C. Young, G. Dong, Chem. Soc. Rev. 44 (2015) 7764-7786;
  (b) X. Chen, K.M. Engle, D.H. Wang, J.Q. Yu, Angew. Chem. Int. Ed. 48 (2009) 5094-5115;
  (c) D. Alberico, M.E. Scott, M. Lautens, Chem. Rev. 107 (2007) 174-238;
  (d) J.A. Labinger, J.E. Bercaw, Nature 417 (2002) 507-514;
  (e) B.D. Dangel, K. Godula, S.W. Youn, B. Sezen, D. Sames, J. Am. Chem. Soc. 124 (2002) 11856.
3. [3]
  (a) T.W. Lyons, M.S. Sanford, Chem. Rev. 110 (2010) 1147-1169;
  (b) O. Daugulis, J. Roane, L.D. Tran, Acc. Chem. Res. 48 (2015) 1053-1064;
  (c) G. He, B. Wang, W.A. Nack, G. Chen, Acc. Chem. Res. 49 (2016) 635-645;
  (d) O. Daugulis, H.Q. Do, D. Shabashov, Acc. Chem. Res. 42 (2009) 1074-1086;
  (e) O. Baudoin, Chem. Soc. Rev. 40 (2011) 4902-4911.
4. [4]
  (a) J.T. Joseph, J.C. Pablo, I.S. Noam, S.S. Melanie, Nature 531 (2016) 220-224;
  (b) G. Rouquet, N. Chatani, Angew. Chem. Int. Ed. 52 (2013) 11726-11743;
  (c) P.M. Vaibhav, J.A. Garcia-Lopez, ChemCatChem 9 (2017) 1149-1156;
  (d) B.J. Knight, J.O. Rothbaum, E.M. Ferreira, Chem. Sci. 7 (2016) 1982-1987;
  (e) Q. Zhang, B.F. Shi, Chin. J. Chem. 37 (2019) 647-656;
  (f) Z. Chen, B. Wang, J. Zhang, et al., Org. Chem. Front. 2 (2015) 1107-1295;
  (g) H. Li, B.J. Li, Z.J. Shi, Catal. Sci. Technol. 1 (2011) 191-206.
5. [5]
  (a) C.H. Jun, H. Lee, J.B. Hong, J. Org. Chem. 62 (1997) 1200-1201;
  (b) R.B. Bedford, S.J. Coles, M.B. Hursthouse, M.E. Limmert, Angew. Chem. Int. Ed. 42 (2003) 112-114;
  (c) F. Mo, G. Dong, Science 345 (2014) 68-72;
  (d) Q.J. Yao, S. Zhang, B.B. Zhan, B.F. Shi, Angew. Chem. Int. Ed. 56 (2017) 6617-6621;
  (e) G. Liao, Q.J. Yao, Z.Z. Zhang, et al., Angew. Chem. Int. Ed. 57 (2018) 3661-3665;
  (f) G. Liao, B. Li, H.M. Chen, et al., Angew. Chem. Int. Ed. 57 (2018) 17151-17155;
  (g) G. Liao, H.M. Chen, Y.N. Xia, et al., Angew. Chem. Int. Ed. 58 (2019) 11464-11468;
  (h) S. Zhang, Q.J. Yao, G. Liao, et al., ACS Catal. 9 (2019) 1956-1961;
  (i) H.M. Chen, S. Zhang, G. Liao, et al., Organometallics 38 (2019) 4022-4028.
6. [6]
  F.L. Zhang, K. Hong, T.J. Li, H. Park, J.Q. Yu, Science 351(2016) 252-256. doi: 10.1126/science.aad7893
7. [7]
  F. Ma, M. Lei, L. Hu, Org. Lett. 18(2016) 2708-2711. doi: 10.1021/acs.orglett.6b01170
8. [8]
  K. Yang, Q. Li, Y. Liu, G. Li, H. Ge, J. Am. Chem. Soc. 138(2016) 12775-12778. doi: 10.1021/jacs.6b08478
9. [9]
  (a) D.T. D. Tang, K.D. Collins, F. Glorius, J. Am. Chem. Soc. 135 (2013) 7450-7453;
  (b) S. Squez-Cespedes, A. Ferry, L. Candish, F. Glorius, Angew. Chem. Int. Ed. 54 (2015) 5772-5776;
  (c) S. Korwar, M. Burkholder, S.E. Gilliland Ⅲ, et al., Chem. Commun. 53 (2017) 7022-7025;
  (d) Y.M. A. Yamada, Y. Yuyama, T. Sato, S. Fujikawa, Y. Uozumi, Angew. Chem. Int. Ed. 53 (2014) 127-131;
  (e) V.A. Zinovyeva, M.A. Vorotyntsev, I. Bezverkhyy, D. Chaumont, J.C. Hierso, Adv. Funct. Mater. 21 (2011) 1064-1075;
10. [10]
  (a) D. Zhang, B. Zhaorigetu, Y.S. Bao, J. Phys. Chem. C 119 (2015) 20426-20432;
  (b) Y.S. Bao, D. Zhang, M. Jia, B. Zhaorigetu, Green Chem. 18 (2016) 2072-2077.
11. [11]
  (a) V.G. Zaitsev, D. Shabashov, O. Daugulis, J. Am. Chem. Soc. 127 (2005) 13154-13155;
  (b) T. Neetipalli, D. Arnab, S. Anurag, et al., Adv. Synth. Catal. 361 (2019) 1441-1446.
12. [12]
  Y. Rozita, R. Brydson, T.P. Comyn, et al. , ChemCatChem 5(2013) 2695-2706. doi: 10.1002/cctc.201200880
13. [13]
  T. Pillo, R. Zimmermann, P. Steiner, S. Hüfner, J. Phys. Condens. Matter 9(1997) 3987-3999.
14. [14]
  K. Hong, H. Park, J.Q. Yu, ACS Catal. 7(2017) 6938-6941. doi: 10.1021/acscatal.7b02905
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通讯作者: 陈斌, bchen63@163.com

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沈阳化工大学材料科学与工程学院沈阳 110142

Nano palladium catalyzed C(sp3)—H bonds arylation by a transient directing strategy

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通讯作者: 陈斌, bchen63@163.com

Nano palladium catalyzed C(sp³)—H bonds arylation by a transient directing strategy