Zn-Mediated Hydrodeoxygenation of Tertiary Alkyl Oxalates

Yang Ye; Guobin Ma; Ken Yao; Hegui Gong

doi:10.1055/a-1328-0352

Synlett, Inhaltsverzeichnis

Synlett 2021; 32(16): 1625-1628
DOI: 10.1055/a-1328-0352

cluster

Modern Nickel-Catalyzed Reactions

Zn-Mediated Hydrodeoxygenation of Tertiary Alkyl Oxalates

Yang Ye

^aSchool of Materials Science and Engineering, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China

,

Guobin Ma

^bCenter for Supramolecular Chemistry and Catalysis, Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China

,

Ken Yao

^aSchool of Materials Science and Engineering, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China

^bCenter for Supramolecular Chemistry and Catalysis, Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China

,

Hegui Gong ∗

^aSchool of Materials Science and Engineering, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China

^bCenter for Supramolecular Chemistry and Catalysis, Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, P. R. of China

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

Herein we describe a general, mild, and scalable method for hydrodeoxygenation of readily accessible tertiary alkyl oxalates by Zn/silane under Ni-catalyzed conditions. The reduction method is suitable for an array of structural motifs derived from tertiary alcohols that bear diverse functional groups, including the synthesis of a key intermediate en route to estrone.

Key words

Zn - silane - hydrodeoxygenation - C–O bonds - oxalates

Volltext

Referenzen

References and Notes

1a Cornella J, Zarate C, Martin R. Chem. Soc. Rev. 2014; 43: 8081
1b Su B, Cao Z.-C, Shi Z.-J. Acc. Chem. Res. 2015; 48: 886
1c Pound SM, Watson MP. Chem. Commun. 2018; 54: 12286
1d Rosen BM, Quasdorf KW, Wilson DA, Zhang N, Resmerita AM, Garg NK, Percec V. Chem. Rev. 2011; 111: 1346
1e Tollefson EJ, Hanna LE, Jarvo ER. Acc. Chem. Res. 2015; 48: 2344

2a Bisz E, Szostak M. ChemSusChem 2017; 10: 3964
2b Sundararaju B, Achard M, Bruneau C. Chem. Soc. Rev. 2012; 41: 4467
2c Liu J, Ye Y, Sessler JL, Gong H. Acc. Chem. Res. 2020; 53: 1833
2d Lu X, Zhang Z.-Q, Lu Y, Zhang B, Wang B, Gong T.-J, Tian C.-L, Xiao B, Fu Y. Chin. J. Chem. 2019; 37: 11

For reviews on aryl–O couplings, see:

3a Tobisu M, Chatani N. Acc. Chem. Res. 2015; 48: 1717
3b Zeng H, Qiu Z, Domínguez-Huerta A, Hearne Z, Chen Z, Li C.-J. ACS Catal. 2017; 7: 510

4a Crich D, Quintero L. Chem. Rev. 1989; 89: 1413
4b McCombie SW, Motherwell WB, Tozer MJ. Org. React. 2012; 77: 161
4c Dolan SC, MacMillan J. J. Chem. Soc., Chem. Commun. 1985; 1588

5a Jamison CR, Overman LE. Acc. Chem. Res. 2016; 49: 1578
5b Nawrat CC, Jamison CR, Slutskyy Y, MacMillan DW. C, Overman LE. J. Am. Chem. Soc. 2015; 137: 11270
5c Lackner GL, Quasdorf KW, Overman LE. J. Am. Chem. Soc. 2013; 135: 15342
5d Gao C, Li J, Yu J, Yang H, Fu H. Chem. Commun. 2016; 52: 7292
5e Zhang X, MacMillan DW. C. J. Am. Chem. Soc. 2016; 138: 13862
5f Rackl D, Kais V, Lutsker E, Reiser O. Eur. J. Org. Chem. 2017; 2130

6 Gao J, Rao P, Xu K, Wang S, Wu Y, He C, Ding H. J. Am. Chem. Soc. 2020; 142: 4592
7 Xu B, Xun W, Su S, Zhai H. Angew. Chem. Int. Ed. 2020; 59: 16475
8 Pan S, Chen S, Dong G. Angew. Chem. Int. Ed. 2018; 57: 6333

9a Ye Y, Chen H, Sessler JL, Gong H. J. Am. Chem. Soc. 2019; 141: 820
9b Gao M, Sun D, Gong H. Org. Lett. 2019; 21: 1645
9c Pan Y, Gong Y, Song Y, Tong W, Gong H. Org. Biomol. Chem. 2019; 17: 4230

10a Álvarez-Bercedo P, Martin R. J. Am. Chem. Soc. 2010; 132: 17352
10b Tobisu M, Yamakawa K, Shimasaki T, Chatani N. Chem. Commun. 2011; 47: 2946
10c Speckmeier E, Padié C, Zeitler K. Org. Lett. 2015; 17: 4818
10d Qin T, Malins LR, Edwards JT, Merchant RR, Novak AJ. E, Zhong JZ, Mille RB, Yan M, Yuan C, Eastgate MD, Baran PS. Angew. Chem. Int. Ed. 2017; 56: 260
10e Sergeev AG, Hartwig JF. Science 2011; 332: 439

11a Ye Y, Chen H, Yao K, Gong H. Org. Lett. 2020; 22: 2070
11b Chen H, Ye Y, Tong W, Fang J, Gong H. Chem. Commun. 2020; 56: 454

For more examples on reductive formation of all-carbon quaternary centers, see:

12a Wang X, Ma G, Peng Y, Pitsch CE, Moll BJ, Ly TD, Wang X, Gong H. J. Am. Chem. Soc. 2018; 140: 14490
12b Chen H, Jia X, Yu Y, Qian Q, Gong H. Angew. Chem. Int. Ed. 2017; 56: 13103
12c Wang X, Wang S, Xue W, Gong H. J. Am. Chem. Soc. 2015; 137: 11562
12d Zhao C, Jia X, Wang X, Gong H. J. Am. Chem. Soc. 2014; 136: 17645
12e Primer DN, Molander GA. J. Am. Chem. Soc. 2017; 139: 9847
12f Green SA, Vásquez-Céspedes S, Shenvi RA. J. Am. Chem. Soc. 2018; 140: 11317
12g Green SA, Huffman TR, McCourt RO, Puyl V, Shenvi RA. J. Am. Chem. Soc. 2019; 141: 7709
12h García-Domínguez A, Li Z, Nevado C. J. Am. Chem. Soc. 2017; 139: 6835
12i Lu X, Wang Y, Zhang B, Pi J.-J, Wang X.-X, Gong T.-J, Xiao B, Fu Y. J. Am. Chem. Soc. 2017; 139: 12632

13a Breitenfeld J, Scopelliti R, Hu X. Organometallics 2012; 31: 2128
13b Cornella J, Gómez-Bengoa E, Martin R. J. Am. Chem. Soc. 2013; 135: 1997

For reviews on cross-electrophile couplings, see:

14a Knappke CE. I, Grupe S, Gärtner D, Corpet M, Gosmini C, Wangelin AJ. Chem. Eur. J. 2014; 20: 6828
14b Moragas T, Correa A, Martin R. Chem. Eur. J. 2014; 20: 8242
14c Weix DJ. Acc. Chem. Res. 2015; 48: 1767
14d Gu J, Wang X, Xue W, Gong H. Org. Chem. Front. 2015; 3: 1411

15a Prévost S, Dupré N, Leutzsch M, Wang Q, Wakchaure V, List B. Angew. Chem. Int. Ed. 2014; 53: 8770
15b Gong Q, Wen J, Zhang X. Chem. Sci. 2019; 10: 6350

16 Reddy BR. P, Chowdhury S, Auffrant A, Gosmini C. Adv. Synth. Catal. 2018; 360: 3026
17 Zhang J, Li Z, Zhuo J, Cui Y, Han T, Li C. J. Am. Chem. Soc. 2019; 141: 8372
18 See the Supporting Information for details.
19 Enev VS, Harre JM, Nickisch K. Tetrahedron: Asymmetry 1998; 9: 2693

Zusatzmaterial

Supporting Information