Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2021; 53(22): 4213-4220
DOI: 10.1055/s-0037-1610779
DOI: 10.1055/s-0037-1610779
special topic
Special Issue dedicated to Prof. Sarah Reisman, recipient of the 2019 Dr. Margaret Faul Women in Chemistry Award
Titanium and Cobalt Bimetallic Radical Redox Relay for the Isomerization of N-Bz Aziridines to Allylic Amides
This work is supported by the National Institute of General Medical Sciences (R01GM134088).
Abstract
Herein a bimetallic radical redox-relay strategy is employed to generate alkyl radicals under mild conditions with titanium(III) catalysis and terminated via hydrogen atom transfer with cobalt(II) catalysis to enact base-free isomerizations of N-Bz aziridines to N-Bz allylic amides. This reaction provides an alternative strategy for the synthesis of allylic amides from alkenes via a three-step sequence to accomplish a formal transpositional allylic amination.
Key words
radical redox relay - titanium catalysis - cobalt catalysis - bimetallic - aziridines - allylic amines - allylic amidesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610779.
- Supporting Information
Primary Data
Primary data for this article are available online at https://zenodo.org/record/5138200 and can be cited using the following DOI: 10.5281/zenodo.5138200.
Publication History
Received: 11 May 2021
Accepted after revision: 24 June 2021
Article published online:
29 July 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Trost B, Krische M, Radinov R, Zanoni G. J. Am. Chem. Soc. 1996; 118: 6297
- 1b Kawatsura M, Hirakawa T, Tanaka T, Ikeda D, Shuichi H, Itoh T. Tetrahedron Lett. 2008; 15: 2450
- 1c Nagano T, Kobayashi S. J. Am. Chem. Soc. 2009; 131: 4200
- 1d Dubovyk I, Watson I, Yudin A. J. Org. Chem. 2013; 78: 1559
- 2a Takeuchi R, Shiga N. Org. Lett. 1999; 1: 265
- 2b Takeuchi R, Ue N, Tanabe K, Yamashita K, Shiga N. J. Am. Chem. Soc. 2001; 123: 9525
- 2c Ohmura T, Hartwig J. J. Am. Chem. Soc. 2002; 124: 15164
- 2d Defieber C, Ariger M, Moriel P, Carreira E. Angew. Chem. Int. Ed. 2007; 46: 3139
- 2e Yang Z, Jiang R, Zheng C, You S. J. Am. Chem. Soc. 2018; 140: 3114
- 2f Kim S, Schwartz L, Zbieg J, Stivala C, Krische M. J. Am. Chem. Soc. 2019; 141: 671
- 3a Overman LE. J. Am. Chem. Soc. 1974; 96: 597
- 3b Xing D, Yang D. Org. Lett. 2010; 12: 1068
- 3c Kirsch SF, Overman LE, Watson MP. J. Org. Chem. 2004; 69: 8101
- 4a Noble A, MacMillan D. J. Am. Chem. Soc. 2014; 136: 11602
- 4b Till N, Smith R, MacMillan D. J. Am. Chem. Soc. 2018; 140: 5701
- 5 Goldfogel M, Roberts C, Meek S. J. Am. Chem. Soc. 2014; 136: 6227
- 6 Yukawa T, Seelig B, Xu Y, Morimoto H, Matsunaga S, Berkessel A, Shibasaki M. J. Am. Chem. Soc. 2010; 132: 11988
- 7 Yi X, Hu X. Angew. Chem. Int. Ed. 2019; 58: 4700
- 8 Bahena E, Griffin S, Schafer L. J. Am. Chem. Soc. 2020; 142: 20566
- 9 Clark J, Roche C. Chem. Commun. 2005; 5175
- 10a Fix S, Brice J, Stahl S. Angew. Chem. Int. Ed. 2002; 41: 164
- 10b Reed S, White C. J. Am. Chem. Soc. 2008; 130: 3316
- 10c McDonald R, Stahl S. Angew. Chem. Int. Ed. 2010; 49: 5529
- 10d Bao H, Tambar U. J. Am. Chem. Soc. 2012; 134: 18495
- 10e Pattillo C, Strambeanu I, Calleja P, Vermeulen N, Mizuno T, White C. J. Am. Chem. Soc. 2016; 138: 1265
- 11a Burman J, Harris R, Farr C, Bacsa J, Blakey S. ACS Catal. 2019; 9: 5474
- 11b Kazerouni A, Nelson T, Chen S, Sharp K, Blakey S. J. Org. Chem. 2019; 84: 13179
- 11c Knecht T, Mondal S, Ye J, Das M, Glorius F. Angew. Chem. Int. Ed. 2019; 58: 7117
- 11d Lei H, Rovis T. J. Am. Chem. Soc. 2019; 141: 2268
- 11e Lei H, Rovis T. Nat. Chem. 2020; 12: 725
- 12a Burman J, Blakey S. Angew. Chem. Int. Ed. 2017; 56: 13666
- 12b Collet F, Lescot C, Liang C, Dauban P. Dalton Trans. 2010; 39: 10401
- 13 Harvey M, Musaev D, Du Bois J. J. Am. Chem. Soc. 2011; 133: 17207
- 14 Hu Y, Lang K, Li C, Gill J, Kim I, Lu H, Fields K, Marshall M, Cheng Q, Cui X, Wojtas L, Zhang P. J. Am. Chem. Soc. 2019; 141: 18160
- 15a Ma Z, Zhou Z, Kurti L. Angew. Chem. Int. Ed. 2017; 56: 9886
- 15b Cheng Q, Zhou Z, Jiang H, Siitonen J, Ess D, Zhang X, Kurti L. Nat. Catal. 2020; 3: 386
- 16 Zhang Z, Scheffold R. Helv. Chim. Acta 1993; 76: 2602
- 17a Gansäuer A, Otte M, Shi L. J. Am. Chem. Soc. 2011; 133: 416
- 17b Yao C, Dahmen T, Gansäuer A, Norton J. Science 2019; 364: 764
- 18a Birmingham JM, Fischer AK, Wilkinson G. Naturwissenschaften 1955; 42: 96
- 18b Natta G, Dall’asta G, Mazzanti G, Gianni U, Cesca S. Angew. Chem. 1959; 71: 205
- 18c Reid A, Wailes P. Aust. J. Chem. 1965; 18: 9
- 18d Green M, Lucas C. Dalton Trans. 1972; 1000
- 19a Nugent WA, RajanBabu TV. J. Am. Chem. Soc. 1988; 110: 8561
- 19b RajanBabu TV, Nugent WA. J. Am. Chem. Soc. 1994; 116: 986
- 20a Gansäuer A, Lauterbach T, Bluhm H, Noltemeyer M. Angew. Chem. Int. Ed. 1999; 38: 2909
- 20b Gansäuer A, Lauterbach T, Geich-Gimbel D. Chem. Eur. J. 2004; 10: 4983
- 20c Congonul A, Behlendorf M, Gansäuer A, van Gastel M. Inorg. Chem. 2013; 52: 11859
- 20d Zhang Z, Richrath R, Gansäuer A. ACS Catal. 2019; 9: 3208
- 21 Hao W, Wu X, Sun J, Siu J, MacMillan S, Lin S. J. Am. Chem. Soc. 2017; 139: 12141
- 22 For a recent review of Ti(III) chemistry, see: McCallum T, Wu X, Lin S. J. Org. Chem. 2019; 84: 14369
- 23a Shevick S, Obradors C, Shenvi R. J. Am. Chem. Soc. 2018; 140: 12056
- 23b Gaspar B, Carreira E. J. Am. Chem. Soc. 2009; 131: 13214
- 23c Li G, Kuo J, Han A, Abuyuan J, Young L, Norton J, Palmer J. J. Am. Chem. Soc. 2016; 138: 7698
- 23d Discolo C, Touney E, Pronin S. J. Am. Chem. Soc. 2019; 141: 17527
- 23e Zhou X, Yang F, Sun H, Yin Y, Ye W, Zhu R. J. Am. Chem. Soc. 2019; 141: 7250
- 23f Song L, Fu N, Ernst BG, Lee WH, Frederick MO, DiStasio JrR. A, Lin S. Nat. Chem. 2020; 12: 747
- 23g Crossley S, Obradors C, Marinez R, Shenvi R. Chem. Rev. 2016; 116: 8912
- 23h Hapke M, Hilt G. Cobalt Catalysis in Organic Synthesis: Methods and Reactions. Wiley; New York: 2020
- 24a Sun X, Chen J, Ritter T. Nat. Chem. 2018; 10: 1229
- 24b Dighe SU, Juliá F, Luridiana A, Douglas JJ, Leonori D. Nature 2020; 584: 75
- 24c West J, Huang D, Sorensen E. Nat. Commun. 2015; 6: 10093
- 25 Hao W, Wu X, Sun J, Siu J, MacMillan S, Lin S. J. Am. Chem. Soc. 2017; 139: 12141
- 26 Zhang Q-Z, Vogelsang E, Qu Z-W, Grimme S, Gansäuer A. Angew. Chem. Int. Ed. 2017; 56: 12654
- 27 Bach R, Dmitrenko O. J. Org. Chem. 2002; 67: 3884
- 28 Ye K-Y, McCallum T, Lin S. J. Am. Chem. Soc. 2019; 141: 9548
- 29 Gansäuer A, Hildebrandt S, Michelmann A, Dahmen T, Laufenberg D, Kube C, Fianu G, Flowers R. Angew. Chem. Int. Ed. 2015; 54: 7003
- 30 Ferraris D, Drury W, Cox C, Lectka T. J. Org. Chem. 1998; 63: 4568
- 31 Gansäuer A, Kube C, Daasbjerg K, Sure R, Grimme S, Fianu G, Sadasivam D, Flowers R. J. Am. Chem. Soc. 2014; 136: 1663
- 32 Daasbjerg K, Svith H, Grimme S, Gerenkamp M, Muck-Lichtenfeld C, Gansäuer A, Barchuk A. Top Curr. Chem. 2006; 263: 39
- 33a Bermejo F, Sandoval C. J. Org. Chem. 2004; 69: 5275
- 33b Fernández-Mateos A, Madrazo SE, Teijón PH, González R. Eur. J. Org. Chem. 2010; 856
- 34 Wu X, Hao W, Ye K-Y, Jiang B, Pombar G, Song Z, Lin S. J. Am. Chem. Soc. 2018; 140: 14836
- 35 Crossley SW. M, Barabé F, Shenvi RA. J. Am. Chem. Soc. 2014; 136: 16788
- 36 Blanksby S, Ellison G. Acc. Chem. Res. 2003; 36: 255
For examples employing Pd catalysis, see:
For recent examples employing Ir catalysis, see:
For examples of Pd-catalyzed allylic amination, see:
For examples of Ir-catalyzed allylic amination, see:
For examples of Rh-catalyzed allylic amination, see:
For other examples of cooperative catalysis featuring Ti, see:
For historical syntheses, see:
For recent examples, see:
For reviews, see:
For recent examples, see: