Palladium-Catalyzed Desulfurative Hiyama Coupling of Thioureas to Achieve Amides via Selective C–N Bond Cleavage

Zhanyu He; Chu Yan; Mei Zhang; Majeed Irfan; Zijia Wang; Zhuo Zeng

doi:10.1055/s-0040-1720907

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(03): 705-710
DOI: 10.1055/s-0040-1720907

paper

Palladium-Catalyzed Desulfurative Hiyama Coupling of Thioureas to Achieve Amides via Selective C–N Bond Cleavage

Zhanyu He

^aSchool of Chemistry, South China Normal University, Guangzhou 510006, P. R. of China

,

Chu Yan

^aSchool of Chemistry, South China Normal University, Guangzhou 510006, P. R. of China

,

Mei Zhang

^aSchool of Chemistry, South China Normal University, Guangzhou 510006, P. R. of China

,

Majeed Irfan

^aSchool of Chemistry, South China Normal University, Guangzhou 510006, P. R. of China

,

Zijia Wang

^aSchool of Chemistry, South China Normal University, Guangzhou 510006, P. R. of China

,

Zhuo Zeng∗

^aSchool of Chemistry, South China Normal University, Guangzhou 510006, P. R. of China

^bKey Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 345 Lingling Road, Shanghai 200032, P. R. of China

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

Palladium-catalyzed Hiyama coupling of active thioureas via selective C–N bond cleavage is reported. Notably, the new approach employed active thioureas as coupling partners in the presence of arylsilanes to give amides in good yield. Further, this strategy, which utilized CuF₂ as a key oxidant and activator, afforded various amide products under mild conditions and an easy to handle procedure without extra base.

Key words

desulfurative Hiyama coupling - CuF₂ activator - thiourea - selective C–N bond cleavage - amide

Volltext

Referenzen

References
1 Greenberg A, Breneman CM, Liebman JF. The Amide Amide Linkage: Structural Significance in Chemistry, Biochemistry, and Materials Science. Wiley; New York: 2000
2 Brown DG, Boström J. J. Med. Chem. 2016; 59: 4443

3a Allen CL, Williams JM. J. Chem. Soc. Rev. 2011; 40: 3405
3b de Figueiredo RM, Suppo J.-S, Campagne J.-M. Chem. Rev. 2016; 116: 12029
3c Dunetz JR, Magano J, Weisenburger GA. Org. Process Res. Dev. 2016; 20: 140
3d Khan WU, Baharudin L, Choi J, Yip AC. K. ChemCatChem 2021; 13: 1
3e Li G, Szostak M. Synthesis 2020; 52: 2579
3f Ojeda-Porras A, Gamba-Sánchez D. J. Org. Chem. 2016; 81: 11548
3g Todorovic M, Perrin DM. Pept. Sci. 2020; 112: e24210
3h Valeur E, Bradley M. Chem. Soc. Rev. 2009; 38: 606

4a Constable DJ. C, Dunn PJ, Hayler JD, Humphrey GR, Leazer JJ. L, Linderman RJ, Lorenz K, Manley J, Pearlman BA, Wells A, Zaks A, Zhang TY. Green Chem. 2007; 9: 411
4b Wu X, Hu L. J. Org. Chem. 2007; 72: 765

5a Buchspies J, Szostak M, Li G, Szostak M. Catalysts 2019; 9: 2579
5b Takise R, Muto K, Yamaguchi J. Chem. Soc. Rev. 2017; 46: 5864

6 Ben Halima T, Vandavasi JK, Shkoor M, Newman SG. ACS Catal. 2017; 7: 2176

7a Li G, Zhou T, Poater A, Cavallo L, Nolan SP, Szostak M. Catal. Sci. Technol. 2020; 10: 710
7b Shi S, Nolan SP, Szostak M. Acc. Chem. Res. 2018; 51: 2589
7c Shi S, Szostak M. Chem. Commun. 2017; 53: 10584
7d Zhou T, Li G, Nolan SP, Szostak M. Org. Lett. 2019; 21: 3304

8 Su J, Li W, Li X, Xu J, Song Q. ChemCatChem 2020; 12: 5664
9 Shakeel A, Altaf AJ. Drug Des. Med. Chem. 2016; 2: 10
10 Hargrave KD, Hess FK, Oliver JT. J. Med. Chem. 1983; 26: 1158
11 Sondhi SM, Sharma VK, Singhal N, Verma RP, Shukla R, Raghubir R, Dubey MP. Phosphorus Sulfur Silicon Relat. Elem. 2000; 156: 21
12 Loev B, Bender PE, Bowman H, Helt A, McLean R, Jen T. J. Med. Chem. 1972; 15: 1024
13 Rosove MH. West. J. Med. 1977; 126: 339
14 Mahanta N, Szantai-Kis DM, Petersson EJ, Mitchell DA. ACS Chem. Biol. 2019; 14: 142
15 Li G, Ma S, Szostak M. Trends Chem. 2020; 2: 914

16a Cui M, Chen Z, Liu T, Wang H, Zeng Z. Tetrahedron Lett. 2017; 58: 3819
16b Cui M, Wu H, Jian J, Wang H, Liu C, Daniel S, Zeng Z. Chem. Commun. 2016; 52: 12076
16c Guo W, Huang J, Wu H, Liu T, Luo Z, Jian J, Zeng Z. Org. Chem. Front. 2018; 5: 2950
16d He Z, Wang Z, Ru J, Wang Y, Liu T, Zeng Z. Adv. Synth. Catal. 2020; 362: 5794
16e Jian J, He Z, Zhang Y, Liu T, Liu L, Wang Z, Wang H, Wang S, Zeng Z. Eur. J. Org. Chem. 2020; 4176
16f Jian J, Wang Z, Chen L, Gu Y, Miao L, Liu Y, Zeng Z. Synthesis 2019; 51: 4078
16g Luo Z, Liu T, Guo W, Wang Z, Huang J, Zhu Y, Zeng Z. Org. Process Res. Dev. 2018; 22: 1188
16h Luo Z, Wu H, Li Y, Chen Y, Nie J, Lu S, Zhu Y, Zeng Z. Adv. Synth. Catal. 2019; 361: 4117
16i Luo Z, Xiong L, Liu T, Zhang Y, Lu S, Chen Y, Guo W, Zhu Y, Zeng Z. J. Org. Chem. 2019; 84: 10559
16j Wu H, Guo W, Daniel S, Li Y, Liu C, Zeng Z. Chem. Eur. J. 2018; 24: 3444
16k Wu H, Li Y, Cui M, Jian J, Zeng Z. Adv. Synth. Catal. 2016; 358: 3876
16l Wu H, Liu T, Cui M, Li Y, Jian J, Wang H, Zeng Z. Org. Biomol. Chem. 2017; 15: 536
16m Xiong L, Deng R, Liu T, Luo Z, Wang Z, Zhu X.-F, Wang H, Zeng Z. Adv. Synth. Catal. 2019; 361: 5383
16n Zhang Y, Wang Z, Tang Z, Luo Z, Wu H, Liu T, Zhu Y, Zeng Z. Eur. J. Org. Chem. 2020; 1620

17 Mai S, Li W, Li X, Zhao Y, Song Q. Nat. Commun. 2019; 10: 5709
18 Nareddy P, Jordan F, Szostak M. Chem. Sci. 2017; 8: 3204
19 Qi Z, Li S.-S, Li L, Qin Q, Yang L.-M, Liang Y.-K, Kang Y, Zhang X.-Z, Ma A.-J, Peng J.-B. Chem. Asian J. 2021; 16: 503
20 Zhou S, Junge K, Addis D, Das S, Beller M. Angew. Chem. Int. Ed. 2009; 48: 9507
21 Yi X, Lei S, Liu W, Che F, Yu C, Liu X, Wang Z, Zhou X, Zhang Y. Org. Lett. 2020; 22: 4583
22 Voronkoy MG, Tsyendorzhieva IP, Rakhlin VI. Russ. J. Org. Chem. 2008; 44: 481
23 Wang Y, Zhu D, Tang L, Wang S, Wang Z. Angew. Chem. Int. Ed. 2011; 50: 8917
24 Baroudi A, Alicea J, Flack P, Kirincich J, Alabugin IV. J. Org. Chem. 2011; 76: 1521

Zusatzmaterial

Supporting Information