Kinetic Study of Disulfonimide-Catalyzed Cyanosilylation of Aldehydes by Using a Method of Progress Rates

Zhipeng Zhang; Martin Klussmann; Benjamin List

doi:10.1055/s-0040-1707129

Synlett, Table of Contents

Synlett 2020; 31(16): 1593-1597
DOI: 10.1055/s-0040-1707129

letter

Kinetic Study of Disulfonimide-Catalyzed Cyanosilylation of Aldehydes by Using a Method of Progress Rates

Zhipeng Zhang ∗

^aSchool of Chemistry and Molecular Engineering, Frontiers Science Center for Materiobiology and Dynamic Chemistry, East China University of Science & Technology, 130 Meilong Road, Shanghai, 200237, P. R. of China Email: zhipengzhang@ecust.edu.cn

^bMax-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany

,

Martin Klussmann

^bMax-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany

,

Benjamin List

^bMax-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, Germany

› Author Affiliations

Abstract

All articles of this category

Abstract

Kinetic study of organic reactions, especially multistep catalytic reactions, is crucial to in-depth understanding of reaction mechanisms. Here we report our kinetic study on the chiral disulfonimide-catalyzed cyanosilylation of an aldehyde, which revealed that two molecules of TMSCN are involved in the rate-determining C–C bond-forming step. In addition, the apparent activation energy, enthalpy of activation, and entropy of activation were deduced through a study of the temperature dependence of the reaction rates. More importantly, a novel and efficient method that makes use of the progress rates was developed to treat kinetic data obtained by continuous monitoring of the progress of a reaction by in situ FTIR.

Key words

kinetics - progress rates - disulfonimides - cyanation - organocatalysis - aldehydes

Full Text

References

References
1 Vogel P, Houk KN. In Organic Chemistry: Theory, Reactivity, and Mechanisms in Modern Synthesis. Wiley-VCH; Weinheim: 2019

2a Nishii Y, Ikeda M, Hayashi Y, Kawauchi S, Miura M. J. Am. Chem. Soc. 2020; 142: 1621
2b Romine AM, Yang KS, Karunananda MK, Chen JS, Engle KM. ACS Catal. 2019; 9: 7626
2c Masson-Makdissi J, Jang YJ, Prieto L, Taylor MS, Lautens M. ACS Catal. 2019; 9: 11808
2d Shevick SL, Obradors C, Shenvi RA. J. Am. Chem. Soc. 2018; 140: 12056
2e Lee CF, Diaz DB, Holownia A, Kaldas SJ, Liew SK, Garrett GE, Dudding T, Yudin AK. Nat. Chem. 2018; 10: 1062
2f Chung R, Vo A, Fokin VV, Hein JE. ACS Catal. 2018; 8: 7889
2g Wendlandt AE, Vangal P, Jacobsen EN. Nature 2018; 556: 447
2h Schreyer L, Kaib PS. J, Wakchaure VN, Obradors C, Properzi R, Lee S, List B. Science 2018; 362: 216

3a Effenberger F. Angew. Chem. Int. Ed. 1994; 33: 1555
3b Effenberger F, Förster S, Wajant H. Curr. Opin. Biotechnol. 2000; 11: 532
3c Gröger H. Adv. Synth. Catal. 2001; 343: 547
3d García-Urdiales E, Alfonso I, Gotor V. Chem. Rev. 2005; 105: 313
3e Sukumaran J, Hanefeld U. Chem. Soc. Rev. 2005; 34: 530
3f Holt J, Hanefeld U. Curr. Org. Synth. 2009; 6: 15

4a Zeng X.-P, Cao Z.-Y, Wang X, Chen L, Zhou F, Zhu F, Wang C.-H, Zhou J. J. Am. Chem. Soc. 2016; 138: 416
4b Laurell Nash A, Hertzberg R, Wen Y.-Q, Dahlgren B, Brinck T, Moberg C. Chem. Eur. J. 2016; 22: 3821
4c Wei Y.-L, Huang W.-S, Cui Y.-M, Yang K.-F, Xu Z, Xu L.-W. RSC Adv. 2015; 5: 3098
4d Lv C, Miao C.-X, Xu D, Wang S, Xia C, Sun W. Catal. Commun. 2012; 27: 138
4e Uemura M, Kurono N, Sakai Y, Ohkuma T. Adv. Synth. Catal. 2012; 354: 2023
4f Wen YQ, Ren WM, Lu XB. Chin. Chem. Lett. 2011; 22: 1285
4g Lv C, Cheng Q, Xu D, Wang S, Xia C, Sun W. Eur. J. Org. Chem. 2011; 3407
4h Zhang Z, Wang Z, Zhang R, Ding K. Angew. Chem. Int. Ed. 2010; 49: 6746
4i North M, Omedes-Pujol M, Williamson C. Chem. Eur. J. 2010; 16: 11367
4j North M, Villuendas P, Williamson C. Tetrahedron 2010; 66: 1915
4k Belokon YN, Clegg W, Harrington RW, Maleev VI, North M, Pujol MO, Usanov DL, Young C. Chem. Eur. J. 2009; 15: 2148
4l Kurono N, Arai K, Uemura M, Ohkuma T. Angew. Chem. Int. Ed. 2008; 47: 6643
4m Zeng B, Zhou X, Liu X, Feng X. Tetrahedron 2007; 63: 5129
4n Liu Y, Liu X, Xin J, Feng X. Synlett 2006; 1085
4o Lundgren S, Wingstrand E, Penhoat M, Moberg C. J. Am. Chem. Soc. 2005; 127: 11592
4p Hatano M, Ikeno T, Miyamoto T, Ishihara K. J. Am. Chem. Soc. 2005; 127: 10776
4q Liu X, Qin B, Zhou X, He B, Feng X. J. Am. Chem. Soc. 2005; 127: 12224
4r Belokon YN, Caveda-Cepas S, Green B, Ikonnikov NS, Khrustalev VN, Larichev VS, Moscalenko MA, North M, Orizu C, Tararov VI, Tasinazzo M, Timofeeva GI, Yashkina LV. J. Am. Chem. Soc. 1999; 121: 3968
4s North M, Orizu C, Tararov VI, Ikonnikov NS, Belokon YN, Hibbs DE, Hursthouse MB, Abdul Malik KM. Chem. Commun. 1998; 387
4t Hamashima Y, Sawada D, Kanai M, Shibasaki M. J. Am. Chem. Soc. 1999; 121: 2641
4u Hamashima Y, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2000; 122: 7412

5a Matsumoto A, Asano K, Matsubara S. Org. Lett. 2019; 21: 2688
5b Kurimoto Y, Nasu T, Fujii Y, Asano K, Matsubara S. Org. Lett. 2019; 21: 2156
5c Provencher BA, Bartelson KJ, Liu Y, Foxman BM, Deng L. Angew. Chem. Int. Ed. 2011; 50: 10565
5d Zuend SJ, Jacobsen EN. J. Am. Chem. Soc. 2007; 129: 15872
5e Peng D, Zhou H, Liu X, Wang L, Chen S, Feng X. Synlett 2007; 2448
5f Qin B, Liu X, Shi J, Zheng K, Zhao H, Feng X. J. Org. Chem. 2007; 72: 2374
5g Tian SK, Deng L. Tetrahedron 2006; 62: 11320
5h Fuerst DE, Jacobsen EN. J. Am. Chem. Soc. 2005; 127: 8964
5i Ryu DH, Corey EJ. J. Am. Chem. Soc. 2005; 127: 5384
5j Wen Y, Huang X, Huang J, Xiong Y, Qin B, Feng X. Synlett 2005; 2445
5k Zhou H, Chen F.-X, Qin B, Feng X, Zhang G. Synlett 2004; 1077
5l Li Y, He B, Feng X, Zhang G. Synlett 2004; 1598
5m Ryu DH, Corey EJ. J. Am. Chem. Soc. 2004; 126: 8106
5n Tian S.-K, Hong R, Deng L. J. Am. Chem. Soc. 2003; 125: 9900
5o Tian SK, Deng L. J. Am. Chem. Soc. 2001; 123: 6195
5p Oku J, Ito N, Inoue S. Makromol. Chem. 1979; 180: 1089

6a Jin F.-Z, Zhao C.-C, Ma H.-C, Chen G.-J, Dong Y.-B. Inorg. Chem. 2019; 58: 9253
6b Li Z, Liu Y, Kang X, Cui Y. Inorg. Chem. 2018; 57: 9786
6c Li J, Ren Y, Qi C, Jiang H. Chem. Commun. 2017; 53: 8223

7a Zeng X.-P, Sun J.-C, Liu C, Ji C.-B, Peng Y.-Y. Adv. Synth. Catal. 2019; 361: 3281
7b Kurono N, Ohkuma T. ACS Catal. 2016; 6: 989
7c Wang W, Liu X, Lin L, Feng X. Eur. J. Org. Chem. 2010; 25: 4751
7d North M, Usanov DL, Young C. Chem. Rev. 2008; 108: 5146
7e Wingstrand E, Lundgren S, Penhoat M, Moberg C. Pure Appl. Chem. 2006; 78: 409
7f Brunel J.-M, Holmes IP. Angew. Chem. Int. Ed. 2004; 43: 2752
7g Gregory RJ. H. Chem. Rev. 1999; 99: 3649

8 Zhang Z, Bae HY, Guin J, Rabalakos C, van Gemmeren M, Leutzsch M, Klussmann M, List B. Nat. Commun. 2016; 7: 12478

9a Blackmond DG. Angew. Chem. Int. Ed. 2005; 44: 4302
9b Mathew JS, Klussmann M, Iwamura H, Valera F, Futran A, Emanuelsson EA. C, Blackmond DG. J. Org. Chem. 2006; 71: 4711
9c Zotova N, Broadbelt LJ, Armstrong A, Blackmond DG. Bioorg. Med. Chem. Lett. 2009; 19: 3934
9d Mower MP, Blackmond DG. ACS Catal. 2018; 8: 5977
9e Dechert-Schmitt A.-M, Garnsey MR, Wisniewska HM, Murray JI, Lee T, Kung DW, Sach N, Blackmond DG. ACS Catal. 2019; 9: 4508
9f Wei B, Sharland JC, Lin P, Wilkerson-Hill SM, Fullilove FA, McKinnon S, Blackmond DG, Davies HM. L. ACS Catal. 2020; 10: 1161

10a Burés J. Angew. Chem. Int. Ed. 2016; 55: 2028
10b Burés J. Angew. Chem. Int. Ed. 2016; 55: 16084
10c Nielsen CD.-T, Burés J. Chem. Sci. 2019; 10: 348

11a Maruyama K, Katagiri T. J. Phys. Org. Chem. 1989; 2: 205
11b Peltzer RM, Gauss J, Eisenstein O, Cascella M. J. Am. Chem. Soc. 2020; 142: 2984

12 Girard C, Kagan HB. Angew. Chem. Int. Ed. 1998; 37: 2922
13 Zhang Z, Klussmann M, List B. ChemRxiv 2020; preprint DOI: 10.26434/chemrxiv.12084768.v1

Supplementary Material

Supporting Information