Synthesis 2024; 56(23): 3653-3659
DOI: 10.1055/s-0040-1720140
paper

Iron-Catalyzed Deboronation/Cyanoalkylation of Vinyl Boronic Acids with Cyclobutanone Ketoximes

Hua-Wei Zhang
a   School of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, P. R. of China
,
Yu-Zhao Wang
a   School of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, P. R. of China
,
Xiu-Fen Cheng
b   College of Chemistry, Chemical Engineering and Materials Science, Institute of Biomedical Sciences, Shandong Normal University, Jinan 250014, P. R. of China
,
Han-Yue Zhang
a   School of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, P. R. of China
,
Zi-Ying Wang
a   School of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, P. R. of China
,
Nuo Xu
a   School of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, P. R. of China
,
Yan-Qi Su
a   School of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, P. R. of China
,
Yan Li
a   School of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, P. R. of China
› Institutsangaben
The authors are grateful to the Taishan Scholar Youth Program of Shandong Province (No. tsqnz20230623), and the Academic Promotion Program of Shandong First Medical University (No. 2019LJ003) for financial support.


Abstract

In this paper, an iron-catalyzed deboronation/cyanoalkylation of vinyl boronic acids for the preparation of distal cyanoalkyl alkenes with vinyl boronic acids as radical acceptor and activator is reported. In this reaction, various cyclobutanone oximes and substituted vinyl boronic acids can be transformed into the corresponding cyanoalkylated alkenes in moderate to good yields under these conditions. Mechanistic studies indicated that a single-electron transfer process may be involved in this transformation.

Supporting Information



Publikationsverlauf

Eingereicht: 06. August 2024

Angenommen nach Revision: 06. September 2024

Artikel online veröffentlicht:
30. September 2024

© 2024. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

    • 1a Fleming FF. Nat. Prod. Rep. 1999; 16: 597
    • 1b Fleming FF, Wang Q. Chem. Rev. 2003; 103: 2035
    • 1c Fleming FF, Yao L, Ravikumar PC, Funk L, Shook BC. J. Med. Chem. 2010; 53: 7902
    • 1d Lopez R, Palomo C. Angew. Chem. Int. Ed. 2015; 54: 13170
    • 1e Li Y, Shang J.-Q, Wang X.-X, Xia W.-J, Yang T, Xin Y, Li Y.-M. Org. Lett. 2019; 21: 2227
    • 2a Makosza M. Chem. Soc. Rev. 2010; 39: 2855
    • 2b Chu X.-Q, Ge D, Shen Z.-L, Loh T.-P. ACS Catal. 2018; 8: 258
    • 2c Wu J, Zhang J.-Y, Gao P, Xu S.-L, Guo L.-N. J. Org. Chem. 2018; 83: 1046
    • 2d Yang L, Gao P, Duan X.-H, Gu Y.-R, Guo L.-N. Org. Lett. 2018; 20: 1034
    • 2e Zhao J.-F, Gao P, Duan X.-H, Guo L.-N. Adv. Synth. Catal. 2018; 360: 1775
    • 2f Boivin J, Fouquet E, Zard SZ. J. Am. Chem. Soc. 1991; 113: 1055
    • 2g Boivin J, Fouquet E, Zard SZ. Tetrahedron Lett. 1991; 32: 4299
    • 2h Yang H.-B, Selander N. Chem. Eur. J. 2017; 23: 1779
    • 2i Jackman MM, Im S, Bohman SR, Lo CC. L, Garrity AL, Castle SL. Chem. Eur. J. 2018; 24: 594
    • 3a Shen X, Zhao J.-J, Yu S. Org. Lett. 2018; 20: 5523
    • 3b Lu X.-Y, Xia Z.-J, Gao A, Liu Q.-L, Jiang R.-C, Liu C.-C. J. Org. Chem. 2021; 86: 8829
    • 4a Yu X.-Y, Zhao Q.-Q, Chen J, Chen J.-R, Xiao W.-J. Angew. Chem. Int. Ed. 2018; 57: 15505
    • 4b Li L, Chen H, Mei M, Zhou L. Chem. Commun. 2017; 53: 11544
    • 5a Werner A, Piguet A. Ber. Dtsch. Chem. Ges. 1904; 37: 4295
    • 5b Werner A, Detscheff T. Ber. Dtsch. Chem. Ges. 1905; 38: 69
    • 5c Jun C.-H. Chem. Soc. Rev. 2004; 33: 610
    • 5d Leemans E, D’hooghe M, De Kimpe N. Chem. Rev. 2011; 111: 3268
    • 5e Li J, Hu Y, Zhang D, Liu Q, Dong Y, Liu H. Adv. Synth. Catal. 2017; 359: 710
    • 6a Zard SZ. Chem. Soc. Rev. 2008; 37: 1603
    • 6b Rykaczewski KA, Wearing ER, Blackmun DE, Schindler CS. Nat. Synth. 2022; 1: 24
    • 6c Zard SZ. ARKIVOC 2024; 202312112
    • 6d Kalsoom I, Bilal M, Kanwal A, Rasool N, Nazeer U, Ciurea C, Neculau AE, Martinescu CC. J. Saudi Chem. Soc. 2024; 28: 101848
    • 7a Zhang J, Wu J, Chang X, Wang P, Xia J, Wu J. Org. Chem. Front. 2022; 9: 917
    • 7b He F.-S, Bao P, Yu F, Zeng L.-H, Deng W.-P, Wu J. Org. Lett. 2021; 23: 7472
    • 8a Xia P.-J, Hu Y.-Z, Ye Z-P, Li X.-J, Xiang H.-Y, Yang H. J. Org. Chem. 2020; 85: 3538
    • 8b Yin Z, Rabeah J, Brückner A, Wu X.-F. ACS Catal. 2018; 8: 10926
    • 8c Nishimura T, Uemura S. J. Am. Chem. Soc. 2000; 122: 12049
    • 8d Nishimura T, Nishiguchi Y, Maeda Y, Uemura S. J. Org. Chem. 2004; 69: 5342
    • 8e Nishimura T, Yoshinaka T, Nishiguchi Y, Maeda Y, Uemura S. Org. Lett. 2005; 7: 2425
    • 8f Gu Y.-R, Duan X.-H, Yang L, Guo L.-N. Org. Lett. 2017; 19: 5908
    • 9a Zhao J.-F, Duan X.-H, Gu Y-R, Gao P, Guo L-N. Org. Lett. 2018; 20: 4614
    • 9b Yu X.-Y, Chen J.-R, Wang P.-Z, Yang M.-N, Liang D, Xiao W.-J. Angew. Chem. Int. Ed. 2018; 57: 738
    • 9c Liu Y, Wang Q.-L, Chen Z, Li H, Xiong B.-Q, Zhang P.-L, Tang K.-W. Chem. Commun. 2020; 56: 3011
    • 9d Zhao X, Ji L, Gao Y, Sun T, Qiao J, Li A, Lu K. J. Org. Chem. 2021; 86: 11399
    • 9e Guin S, MaJee D, Samanta S. Asian J. Org. Chem. 2021; 10: 1595
    • 9f Zhou N, Wu S, Kuang K, Xia Z, Xu Q, Zhang M. Org. Chem. Front. 2021; 8: 6032
    • 9g Guan T, Guo J.-Y, Zhang Q.-H, Xu X.-W, Yu X.-Y, Zhang Y, Zhao K. Green Chem. 2022; 24: 6524
  • 11 Fleming FF, Zhang Z. Tetrahedron 2005; 61: 747
  • 14 Xia P.-J, Ye Z.-P, Hu Y.-Z, Song D, Xiang H.-Y, Chen X.-Q, Yang H. Org. Lett. 2019; 21: 2658
    • 15a Xia X, Chen X, Zhao B, Yuan Y. Tetrahedron 2023; 130: 133179
    • 15b Shi D, Xia X, Zhao B, Yuan Y. Org. Biomol. Chem. 2023; 21: 6298
    • 16a Zhao B, Shi Z. Angew. Chem. Int. Ed. 2017; 56: 12727
    • 16b Yang H.-B, Pathipati SR, Selander N. ACS Catal. 2017; 7: 8441