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Synthesis 2014; 46(12): 1583-1592
DOI: 10.1055/s-0033-1341152
DOI: 10.1055/s-0033-1341152
practical synthetic procedures
The Cobalt-Catalyzed Cross-Coupling Reaction of Alkyl Halides with Alkyl Grignard Reagents: A New Route to Constructing Quaternary Carbon Centers
Weitere Informationen
Publikationsverlauf
Received: 10. Februar 2014
Accepted after revision: 20. März 2014
Publikationsdatum:
14. Mai 2014 (online)
Abstract
The cross-coupling of alkyl (pseudo)halides with alkyl Grignard reagents is catalyzed efficiently by a cobalt(II) chloride–lithium iodide–1,3-diene catalytic system, which provides a new synthetic tool for constructing sp3 carbon chains. This system is particularly useful for creating quaternary carbon centers via the use of tertiary alkyl Grignard reagents. Various functional groups including esters, amides and carbamates are well tolerated.
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References
- 1a Cárdenas DJ. Angew. Chem. Int. Ed. 2003; 42: 384
- 1b Netherton MR, Fu GC. Adv. Synth. Catal. 2004; 346: 1525
-
1c Frisch AC, Beller M. Angew. Chem. Int. Ed. 2005; 44: 674
- 1d Kambe N, Iwasaki T, Terao J. Chem. Soc. Rev. 2011; 40: 4937
- 1e Hu XL. Chem. Sci. 2011; 2: 1867
- 2a Tamao K, Kiso Y, Sumitani K, Kumada M. J. Am. Chem. Soc. 1972; 94: 9268
- 2b Kiso Y, Tamao K, Kumada M. J. Organomet. Chem. 1973; 50: C12
- 2c Hayashi T, Konishi M, Yokota K.-i, Kumada M. Chem. Lett. 1980; 767
- 3a Burns DH, Miller JD, Chan H.-K, Delaney MO. J. Am. Chem. Soc. 1997; 119: 2125
- 3b Donkervoort JG, Vicario JL, Jastrzebski JT. B. H, Gossage RA, Cahiez G, van Koten G. J. Organomet. Chem. 1998; 558: 61
- 3c Cahiez G, Chaboche C, Jézéquel M. Tetrahedron 2000; 56: 2733
- 3d Terao J, Ikumi A, Kuniyasu H, Kambe N. J. Am. Chem. Soc. 2003; 125: 5646
- 3e Terao J, Todo H, Begum SA, Kuniyasu H, Kambe N. Angew. Chem. Int. Ed. 2007; 46: 2086
- 3f Cahiez G, Gager O, Buendia J. Synlett 2010; 299
- 3g Yang C.-T, Zhang Z.-Q, Liang J, Liu J.-H, Lu X.-Y, Chen H.-H, Liu L. J. Am. Chem. Soc. 2012; 134: 11124
- 3h Ren P, Stern L.-A, Hu XL. Angew. Chem. Int. Ed. 2012; 51: 9110
- 4a Terao J, Kambe N. Bull. Chem. Soc. Jpn. 2006; 79: 663
- 4b Terao J, Kambe N. Acc. Chem. Res. 2008; 41: 1545
- 4c Terao J, Watanabe H, Ikumi A, Kuniyasu H, Kambe N. J. Am. Chem. Soc. 2002; 124: 4222
- 4d Terao J, Naitoh Y, Kuniyasu H, Kambe N. Chem. Lett. 2003; 32: 890
- 4e Terao J, Todo H, Watanabe H, Ikumi A, Kambe N. Angew. Chem. Int. Ed. 2004; 43: 6180
- 4f Terao J, Naitoh Y, Kuniyasu H, Kambe N. Chem. Commun. 2007; 825
- 4g Singh SP, Terao J, Kambe N. Tetrahedron Lett. 2009; 50: 5644
- 4h Singh SP, Iwasaki T, Terao J, Kambe N. Tetrahedron Lett. 2011; 52: 774
- 4i Iwasaki T, Tsumura A, Omori T, Kuniyasu H, Terao J, Kambe N. Chem. Lett. 2011; 40: 1024
- 4j Shen R, Iwasaki T, Terao J, Kambe N. Chem. Commun. 2012; 48: 9313
- 4k Iwasaki T, Higashikawa K, Reddy VP, Ho WW. S, Fujimoto Y, Fukase K, Terao J, Kuniyasu H, Kambe N. Chem. Eur. J. 2013; 19: 2956
- 4l For the alkylation of 2-methylthiobenzothiazoles, see: Ghaderi A, Iwasaki T, Fukuoka A, Terao J, Kambe N. Chem. Eur. J. 2013; 19: 2951
- 5 Iwasaki T, Takagawa H, Singh SP, Kuniyasu H, Kambe N. J. Am. Chem. Soc. 2013; 135: 9604
- 6a Shinokubo H, Oshima K. Eur. J. Org. Chem. 2004; 2081
- 6b Yorimitsu H, Oshima K. Pure Appl. Chem. 2006; 78: 441
- 6c Gosmini C, Bégouin J.-M, Moncomble A. Chem. Commun. 2008; 3221
-
6d Cahiez G, Moyeux A. Chem. Rev. 2010; 110: 1435
- 7a Cahiez G, Chaboche C, Duplais C, Giulliani A, Moyeux A. Adv. Synth. Catal. 2008; 350: 1484
- 7b Zhou W, Napoline JW, Thomas CM. Eur. J. Inorg. Chem. 2011; 2029
- 7c Tsuji T, Yorimitsu H, Oshima K. Angew. Chem. Int. Ed. 2002; 41: 4137
- 7d Ohmiya H, Tsuji T, Yorimitsu H, Oshima K. Chem. Eur. J. 2004; 10: 5640
- 7e Someya H, Ohmiya H, Yorimitsu H, Oshima K. Org. Lett. 2007; 9: 1565
- 7f Someya H, Ohmiya H, Yorimitsu H, Oshima K. Tetrahedron 2007; 63: 8609
- 8 Pangborn AM, Giardello MA, Grubbs RH, Rosen RK, Timmers FJ. Organometallics 1996; 15: 1518
- 9 Green TW, Wuts PG. M. Protective Groups in Organic Synthesis . 4th ed. Wiley; New York: 2006
For representative reviews, see:
For reviews on Co-catalyzed C–C bond forming reactions, see:
For Co-catalyzed C–C bond formation between sp3 carbon centers, see:
For examples with allylic and benzylic nucleophiles, see: