Subscribe to RSS
DOI: 10.1055/s-0040-1706602
Vitamin B12-Catalyzed Dicarbofunctionalization of Bromoalkenes Under Visible Light Irradiation
Financial support for this work was provided by the Foundation for Polish Sciences (FNP TEAM POIR.04.04.00-00-4232/17-00).
Dedicated to Professor Grzegorz Mlostoń on the occasion of his 70th birthday.
Abstract
Vitamin B12 plays a crucial role in enzymatic transformations. This natural compound proved also useful as a catalyst in numerous organic reactions. Commercial availability and lower cost than precious metal complexes, make cobalamin an attractive candidate for a broader use as a benign Co-catalyst. Herein, the vitamin B12-catalyzed dicarbofuntionalization of bromoalkenes with electrophilic olefins is reported leading to substituted pyrrolidines and piperidines in decent yields after only 15 minutes under light irradiation.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706602.
- Supporting Information
Publication History
Received: 31 August 2020
Accepted after revision: 02 November 2020
Article published online:
23 November 2020
© 2020. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Banerjee R. Chemistry and Biochemistry of B12. Wiley; New York: 1999
- 1b Schneider Z, Stroinski A. Comprehensive B12. Walter de Gruyter; Berlin: 1987
- 1c Jones AR. Photochem. Photobiol. Sci. 2017; 16: 820
- 2 Chen Y, Zhang XP. J. Org. Chem. 2004; 69: 2431
- 3 Komeyama K, Ohata R, Kiguchi S, Osaka I. Chem. Commun. 2017; 53: 6401
- 4a Wood JM, Kennedy FS, Wolfe RS. Biochemistry 1968; 7: 1707
- 4b Kennedy FS, Buckman T, Wood JM. Biochim. Biophys. Acta 1969; 177: 661
- 5 Giedyk M, Turkowska J, Lepak S, Marculewicz M, óProinsias K, Gryko D. Org. Lett. 2017; 19: 2670
- 6 Ociepa M, Wierzba AJ, Turkowska J, Gryko D. J. Am. Chem. Soc. 2020; 142: 5355
- 7 Giedyk M, Goliszewska K, Gryko D. Chem. Soc. Rev. 2015; 44: 3391
- 8a Schrauzer GN. Acc. Chem. Res. 1968; 1: 97
- 8b Halpern J. Science 1985; 227: 869
- 8c Demarteau J, Debuigne A, Detrembleur C. Chem. Rev. 2019; 119: 6906
- 9a Nóbrega L, Dinis-Oliveira RJ. Drug Metab. Rev. 2018; 50: 125
- 9b Khan MK, Wang D, Moloney MG. Synthesis 2020; 52: 1602
- 10a Olivier WJ, Smith JA, Bissember AC. Org. Biomol. Chem. 2018; 16: 1216
- 10b Babazadeh M, Soleimani-Amiri S, Vessally E, Hosseinian A, Edjlali L. RSC Adv. 2017; 7: 43716
- 11a Rowlands GJ. Annu. Rep. Prog. Chem., Sect. B: Org. Chem. 2013; 109: 88
- 11b Kwiatkowski MR, Alexanian EJ. Acc. Chem. Res. 2019; 52: 1134
- 12 Rai L, Hassner A. Heterocycles 1990; 30: 817
- 13a Fujioka T, Nakamura T, Yorimitsu H, Oshima K. Org. Lett. 2002; 4: 2257
- 13b Affo W, Ohmiya H, Fujioka T, Ikeda Y, Nakamura T, Yorimitsu H, Oshima K, Imamura Y, Mizuta T, Miyoshi K. J. Am. Chem. Soc. 2006; 128: 8068
- 14a Weiss ME, Kreis LM, Lauber A, Carreira EM. Angew. Chem. Int. Ed. 2011; 50: 11125
- 14b Weiss ME, Carreira EM. Angew. Chem. Int. Ed. 2011; 50: 11501
- 15 Sun Q, Yoshikai N. Org. Lett. 2019; 21: 5238
- 16 Devery JJ, Nguyen JD, Dai C, Stephenson CR. J. ACS Catal. 2016; 6: 5962
- 17 Proinsias KO, Jackowska A, Radzewicz K, Giedyk M, Gryko D. Org. Lett. 2018; 20: 296
- 18 Potrząsaj A, Ociepa M, Baka O, Spólnik G, Gryko D. Eur. J. Org. Chem. 2020; 1567
- 19 Hwang JY, Baek JH, Shin TI, Shin JH, Oh JW, Kim KP, You Y, Kang EJ. Org. Lett. 2016; 18: 4900
- 20 Qi X, Diao T. ACS Catal. 2020; 10: 8542
- 21 Iwamoto H, Akiyama S, Hayama K, Ito H. Org. Lett. 2017; 19: 2614
- 22 Kuang Y, Wang X, Anthony D, Diao T. Chem. Commun. 2018; 54: 2558
- 23 Kwiatkowski MR, Alexanian EJ. Angew. Chem. Int. Ed. 2018; 57: 16857
- 24 Venning AR. O, Kwiatkowski MR, Roque Peña JE, Lainhart BC, Guruparan AA, Alexanian EJ. J. Am. Chem. Soc 2017; 139: 11595
- 25 Bloome KS, McMahen RL, Alexanian EJ. J. Am. Chem. Soc. 2011; 133: 20146
- 26 Tsuji H, Yamagata K, Itoh Y, Endo K, Nakamura M, Nakamura E. Angew. Chem. Int. Ed. 2007; 46: 8060
- 27 Liu H, Qiao Z, Jiang X. Org. Biomol. Chem. 2012; 10: 7274
- 28 Verendel JJ, Zhou T, Li J.-Q, Paptchikhine A, Lebedev O, Andersson PG. J. Am. Chem. Soc. 2010; 132: 8880
- 29 Martínez C, Muñiz K. Angew. Chem. Int. Ed. 2015; 54: 8287
- 30 Kim H, Lee C. Org. Lett. 2011; 13: 2050