Palladium-Catalyzed Hydroalkylation of Alkoxyallenes Using Monofluorinated Nucleophiles

Ling Liao; Zhi-Peng Zhao; Bo-Ning Gu; Jin-Sheng Yu; Jian Zhou

doi:10.1055/a-2096-6929

Synthesis, Inhaltsverzeichnis

Synthesis 2023; 55(19): 3090-3103
DOI: 10.1055/a-2096-6929

paper

Special Issue Honoring Prof. Guoqiang Lin's Contributions to Organic Chemistry

Palladium-Catalyzed Hydroalkylation of Alkoxyallenes Using Monofluorinated Nucleophiles

Ling Liao

^aShanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University, Shanghai 200062, P. R. of China

,

Zhi-Peng Zhao

^aShanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University, Shanghai 200062, P. R. of China

,

Bo-Ning Gu

^aShanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University, Shanghai 200062, P. R. of China

,

Jin-Sheng Yu∗

^aShanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University, Shanghai 200062, P. R. of China

^bHubei Key Laboratory of Quality Control of Characteristic Fruits and Vegetables, Hubei Engineering University, Xiaogan 432000, P. R. of China

,

Jian Zhou

^aShanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University, Shanghai 200062, P. R. of China

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

A branch-selective hydroalkylation of alkoxyallenes with monofluorinated nucleophiles was developed using palladium catalysis, allowing construction of valuable α-monofluoroalkylated allylic ethers. Notably, this represents the first catalytic hydrofluoroalkylation of alkoxyallenes. The practicability of this method is highlighted by its broad substrate scope and diversified product elaborations. Initial investigation of the asymmetric variant could afford chiral fluorine-containing allylic ethers with up to 68% ee.

Key words

palladium catalysis - alkoxyallenes - hydrofluoroalkylation - branch-selectivity - fluorine

Volltext

Referenzen

References

For leading books, see:

1a Hiyama T. Organofluorine Compounds: Chemistry and Applications. Springer; New York: 2000
1b Bégué J.-P, Bonnet-Delpon D. Bioorganic and Medicinal Chemistry of Fluorine . Wiley; Hoboken: 2007
1c Ojima I. Fluorine in Medicinal Chemistry and Chemical Biology. Wiley-Blackwell; Chichester: 2009
1d Reddy VP. Organofluorine Compounds in Biology and Medicine. Elsevier; Amsterdam: 2020

For selected reviews, see:

1e Hagmann WK. J. Med. Chem. 2008; 51: 4359
1f Purser S, Moore PR, Swallow S, Gouverneur V. Chem. Soc. Rev. 2008; 37: 320
1g O’Hagan D. Chem. Soc. Rev. 2008; 37: 308
1h Wang J, Sánchez-Roselló M, Aceña JL, del Pozo C, Sorochinsky AE, Fustero S, Soloshonok VA, Liu H. Chem. Rev. 2014; 114: 2432
1i Müller K, Faeh C, Diederich F. Science 2007; 317: 1881

Selected reviews:

2a Uneyama K, Katagiri T, Amii H. Acc. Chem. Res. 2008; 41: 817
2b Nie J, Guo H.-C, Cahard D, Ma J.-A. Chem. Rev. 2011; 111: 455
2c Furuya T, Kamlet AS, Ritter T. Nature 2011; 473: 470
2d Merino E, Nevado C. Chem. Soc. Rev. 2014; 43: 6598
2e Chu L, Qing F.-L. Acc. Chem. Res. 2014; 47: 1513
2f Charpentier J, Früh N, Togni A. Chem. Rev. 2015; 115: 650
2g Ni C, Hu M, Hu J. Chem. Rev. 2015; 115: 765
2h Alonso C, Martínez de Marigorta E, Rubiales G, Palacios F. Chem. Rev. 2015; 115: 1847
2i Liu X, Xu C, Wang M, Liu Q. Chem. Rev. 2015; 115: 683
2j Zhu Y, Han J, Wang J, Shibata N, Sodeoka M, Soloshonok VA, Coelho JA. S, Toste FD. Chem. Rev. 2018; 118: 3887
2k Hu J, Zhang W, Wang F. Chem. Commun. 2009; 7465
2l Feng Z, Xiao Y.-L, Zhang X. Acc. Chem. Res. 2018; 51: 2264
2m Dilman AD, Levin VV. Acc. Chem. Res. 2018; 51: 1272

3a Chatterjee T, Iqbal N, You Y, Cho EJ. Acc. Chem. Res. 2016; 49: 2284
3b Barata-Vallejo S, Cooke MV, Postigo A. ACS Catal. 2018; 8: 7287
3c Yerien DE, Barata-Vallejo S, Postigo A. Chem. Eur. J. 2017; 23: 14676
3d Koike T, Akita M. Chem 2018; 4: 409
3e Laishram RD, Chen J, Fan B. Chem. Rec. 2021; 21: 69

4a Zimmer R, Reissig H.-U. Chem. Soc. Rev. 2014; 43: 2888
4b Koschker P, Breit B. Acc. Chem. Res. 2016; 49: 1524
4c Blieck R, Taillefer M, Monnier F. Chem. Rev. 2020; 120: 13545
4d Li G.-L, Huo X.-H, Jiang X.-Y, Zhang W.-B. Chem. Soc. Rev. 2020; 49: 2060

5a Yu C.-R, Xu L.-H, Tu S, Li Z.-N, Li B. J. Fluorine Chem. 2006; 127: 1540
5b Cocco M, Pellegrini C, Martínez-Banaclocha H, Giorgis M, Marini E, Costale A, Miglio G, Fornai M, Antonioli L, López-Castejón G, Tapia-Abellán A, Angosto D, Hafner-Bratkovič I, Regazzoni L, Blandizzi C, Pelegrín P, Bertinaria M. J. Med. Chem. 2017; 60: 3656

6a Trost BM, Jäkel C, Plietker B. J. Am. Chem. Soc. 2003; 125: 4438
6b Trost BM, Xie J, Sieber JD. J. Am. Chem. Soc. 2011; 133: 20611
6c Zhou H, Wei Z, Zhang J.-L, Yang H.-M, Xia C.-G, Jiang G.-X. Angew. Chem. Int. Ed. 2017; 56: 1077
6d Jang D.-J, Lee S, Lee J, Moon D, Rhee YH. Angew. Chem. Int. Ed. 2021; 60: 22166
6e Lin H.-C, Knox GJ, Pearson CM, Yang C, Carta V, Snaddon TN. Angew. Chem. Int. Ed. 2022; 61: e202201753
6f Zhu M.-H, Zhang Q.-L, Zi W.-W. Angew. Chem. Int. Ed. 2021; 60: 6545
6g Zhu M.-H, Wang P.-X, Zhang Q.-L, Tang W.-J, Zi W.-W. Angew. Chem. Int. Ed. 2022; 61: e202207621

7a Kinderman SS, de Gelder R, van Maarseveen JH, Schoemaker HE, Hiemstra H, Rutjes FP. J. T. J. Am. Chem. Soc. 2004; 126: 4100
7b Kim H, Lim W, Im D, Kim D, Rhee YH. Angew. Chem. Int. Ed. 2012; 51: 12055
7c Kim H, Rhee YH. J. Am. Chem. Soc. 2012; 134: 4011
7d Bernar I, Fiser B, Blanco-Ania D, Gómez-Bengoa E, Rutjes FP. J. T. Org. Lett. 2017; 19: 4211
7e Jang SH, Kim HW, Jeong W, Moon D, Rhee YH. Org. Lett. 2018; 20: 1248
7f Alonso JM, Muñoz MP. Org. Lett. 2019; 21: 7639
7g Gao Z, Yan C.-X, Qian J.-L, Yang H.-M, Zhou P.-P, Zhang J.-L, Jiang G.-X. ACS Catal. 2021; 11: 6931

8a Cui D.-M, Zheng Z.-L, Zhang C. J. Org. Chem. 2009; 74: 1426
8b Lim W, Kim J, Rhee YH. J. Am. Chem. Soc. 2014; 136: 13618
8c Jiang L.-Y, Jia T, Wang M, Liao J, Cao P. Org. Lett. 2015; 17: 1070

9 Yang Z.-P, Wang J. Angew. Chem. Int. Ed. 2021; 60: 27288

10a Hu X.-S, He J.-X, Dong S.-Z, Zhao Q.-H, Yu J.-S, Zhou J. Nat. Commun. 2020; 11: 5500
10b Hu X.-S, He J.-X, Zhang Y, Zhou J, Yu J.-S. Chin. J. Chem. 2021; 39: 2227
10c Liao L, Zhang Y, Wu Z.-W, Ye Z.-T, Zhang X.-X, Yu J.-S. Chem. Sci. 2022; 13: 12519

11a Inoue M, Sumii Y, Shibata N. ACS Omega 2020; 5: 10633
11b Ogawa Y, Tokunaga E, Kobayashi O, Hirai K, Shibata N. iScience 2020; 23: 101467

12a Emerging Fluorinated Motifs: Synthesis, Properties, and Applications, 1st ed. Cahard D, Ma J.-A. Wiley-VCH; Weinheim: 2020
12b Ni C, Zhu L, Hu J. Acta Chim. Sin. 2015; 73: 90
12c Harsanyi A, Sandford G. Org. Process Res. Dev. 2014; 18: 981

13 Xu P.-W, Huang Z. Nat. Chem. 2021; 13: 634

Selected reviews:

14a Alba A.-NR, Companyó X, Rios R. Chem. Soc. Rev. 2010; 39: 2018
14b Shibata N. Bull. Chem. Soc. Jpn. 2016; 89: 1307
14c Reichel M, Karaghiosoff K. Angew. Chem. Int. Ed. 2020; 59: 12268

Seminal works on the synthesis and application of FBSM:

15a Fukuzumi T, Shibata N, Sugiura M, Yasui H, Nakamura S, Toru T. Angew. Chem. Int. Ed. 2006; 45: 4973
15b Ni C, Li Y, Hu J. J. Org. Chem. 2006; 71: 6829

For selected examples, see:

15c Mizuta S, Shibata N, Goto Y, Furukawa T, Nakamura S, Toru T. J. Am. Chem. Soc. 2007; 129: 6394
15d Furukawa T, Shibata N, Mizuta S, Nakamura S, Toru T, Shiro M. Angew. Chem. Int. Ed. 2008; 47: 8051
15e Alba A.-N, Companyó X, Moyano A, Rios R. Chem. Eur. J. 2009; 15: 7035
15f Zhang S, Zhang Y, Ji Y, Li H, Wang W. Chem. Commun. 2009; 4886
15g Ullah F, Zhao G.-L, Deiana L, Zhu M, Dziedzic P, Ibrahem I, Hammar P, Sun J, Córdova A. Chem. Eur. J. 2009; 15: 10013
15h Liu W.-B, Zheng S.-C, He H, Zhao X.-M, Dai L.-X, You S.-L. Chem. Commun. 2009; 6604

16a Chai W.-W, Guo B, Zhang Q.-L, Zi W.-W. Chem Catal. 2022; 2: 1428

Also see a review:

16b Wei L, Xiong H, Hsung RP. Acc. Chem. Res. 2003; 36: 773

Zusatzmaterial

Supporting Information