Alkylcarbagermatranes Permit an Alkylation-Terminated Catellani Reaction

Abstract

We highlight our recent researches on an alkylation-terminated Catellani reaction using alkylcarbagermatranes. This strategy highlights the unique structure and property of alkylcarbagermatranes and also fills the gap in the Catellani reaction where alkylation termination was missing.

Key words

organogermanium compounds - carbagermatranes - ­Catellani reaction - cross-coupling

Publikationsverlauf

Eingereicht: 28. Januar 2021

Angenommen nach Revision: 17. Februar 2021

Artikel online veröffentlicht:
01. April 2021

• References

• 1a Ye J, Lautens M. Nat. Chem. 2015; 7: 863
• 1b Della Ca’ N, Fontana M, Motti E, Catellani M. Acc. Chem. Res. 2016; 49: 1389
• 1c Wang J, Dong G. Chem. Rev. 2019; 119: 7478
• 2 Catellani M, Frignani F, Rangoni A. Angew. Chem. Int. Ed. 1997; 36: 119
• 3 Catellani M, Motti E, Minari M. Chem. Commun. 2000; 157
• 4 Motti E, Rossetti M, Bocelli G, Catellani M. J. Organomet. Chem. 2004; 689: 3741
• 5 Wilhelm T, Lautens M. Org. Lett. 2005; 7: 4053
• 6a Motti E, Ippomei G, Deledda S, Catellani M. Synthesis 2003; 2671
• 6b Motti E, Mignozzi A, Catellani M. J. Mol. Catal. A: Chem. 2003; 204: 115
• 7 Dong Z, Dong G. J. Am. Chem. Soc. 2013; 135: 18350
• 8a Dong Z, Wang J, Ren Z, Dong G. Angew. Chem. Int. Ed. 2015; 54: 12664
• 8b Huang Y, Zhu R, Zhao K, Gu Z. Angew. Chem. Int. Ed. 2015; 54: 12669
• 8c Zhou P.-X, Ye Y.-Y, Liu C, Zhao L.-B, Hou J.-Y, Chen D.-Q, Tang Q, Wang A.-Q, Zhang J.-Y, Huang Q.-X. ACS Catal. 2015; 5: 4927
• 9a Zhang B.-S, Hua H.-L, Gao L.-Y, Liu C, Qiu Y.-F, Zhou P.-X, Zhou Z.-Z, Zhao J.-H, Liang Y.-M. Org. Chem. Front. 2017; 4: 1376
• 9b Zhang B.-S, Li Y, An Y, Zhang Z, Liu C, Wang X.-G, Liang Y.-M. ACS Catal. 2018; 8: 11827
• 10 Wilson JE. Tetrahedron Lett. 2016; 57: 5053
• 11 Wang J, Dong Z, Yang C, Dong G. Nat. Chem. 2019; 11: 1106
• 12 Jiang W.-T, Xu M.-Y, Yang S, Xie X.-Y, Xiao B. Angew. Chem. Int. Ed. 2020; 59: 20450

For recent research on carbagermatranes, see:
• 13a Jiang W.-T, Yang S, Xu M.-Y, Xie X.-Y, Xiao B. Chem. Sci. 2020; 11: 488
• 13b Xu M.-Y, Jiang W.-T, Li Y, Xu Q.-H, Zhou Q.-L, Yang S, Xiao B. J. Am. Chem. Soc. 2019; 141: 7582

For recent research on other organogermanes, see:
• 14a Fricke C, Deckers K, Schoenebeck F. Angew. Chem. Int. Ed. 2020; 59: 18717
• 14b Sherborne GJ, Gevondian AG, Funes-Ardoiz I, Dahiya A, Fricke C, Schoenebeck F. Angew. Chem. Int. Ed. 2020; 59: 15543
• 14c Dahiya A, Fricke C, Schoenebeck F. J. Am. Chem. Soc. 2020; 142: 7754
• 14d Fricke C, Sherborne GJ, Funes-Ardoiz I, Senol E, Guven S, Schoenebeck F. Angew. Chem. Int. Ed. 2019; 58: 17788
• 14e Fricke C, Dahiya A, Reid WB, Schoenebeck F. ACS Catal. 2019; 9: 9231 corrigendum: ACS Catal. 2019, 9, 10232
• 15 Evans GB, Furneaux RH, Gravestock MB, Lynch GP, Scott GK. Bioorg. Med. Chem. 1999; 7: 1953