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Synthesis 2021; 53(24): 4662-4671
DOI: 10.1055/a-1559-3384
DOI: 10.1055/a-1559-3384
paper
Regioselective Iodine/Zinc Exchange for the Selective Functionalization of Polyiodinated Arenes and Heterocycles in Toluene
We thank the Deutsche Forschungsgemeinschaft (DFG) and Ludwig-Maximilians-Universität München for financial support.
Abstract
Regioselective I/Zn-exchange reactions were performed on polyiodinated arenes or heterocycles within 20 minutes at 0–25 °C using the bimetallic combination pTol2Zn·2LiOR [R = (CH2)2N(Me)(CH2)2NMe2] in toluene. The resulting diaryl- or diheteroarylzincs reacted well with allylic bromides and acyl chlorides to provide functionalized (hetero)aryl iodides in good yields.
Key words
alkoxides - apolar solvents - arenes - heterocycles - lithium - regioselective iodine/zinc exchange - zincSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1559-3384.
- Supporting Information
Publication History
Received: 05 July 2021
Accepted after revision: 27 July 2021
Accepted Manuscript online:
27 July 2021
Article published online:
24 August 2021
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References
- 1a Schröter S, Stock C, Bach T. Tetrahedron 2005; 61: 2245
- 1b Fairlamb IJ. S. Chem. Soc. Rev. 2007; 36: 1036
- 1c Legault CY, Garcia Y, Merlic CA, Houk KN. J. Am. Chem. Soc. 2007; 129: 12664
- 1d Garcia Y, Schoenebeck F, Legault CY, Merlic CA, Houk KN. J. Am. Chem. Soc. 2009; 131: 6632
- 1e Diehl CJ, Scattolin T, Englert U, Schoenebeck F. Angew. Chem. Int. Ed. 2019; 58: 211 ; Angew. Chem. 2019, 131, 217
- 1f Keaveney ST, Kundu G, Schoenebeck F. Angew. Chem. Int. Ed. 2018; 57: 12573 ; Angew. Chem. 2018, 130, 12753
- 1g Diemer V, Leroux FR, Colobert F. Eur. J. Org. Chem. 2011; 327
- 2a McGrath NA, Brichacek M, Njardarson JT. J. Chem. Educ. 2010; 87: 1348
- 2b Brown DG, Boström J. J. Med. Chem. 2016; 59: 4443
- 2c Koo JH, Maynard HD. Chem. Soc. Rev. 2018; 47: 8998
- 3a Transition Metals for Organic Synthesis . Beller M, Bolm C. Wiley-VCH; Weinheim: 2004
- 3b Handbook of Functionalized Organometallics: Applications in Synthesis. Knochel P. Wiley-VCH; Weinheim: 2005
- 4a Negishi E, Huang Z, Wang G, Mohan S, Wang C, Hattori H. Acc. Chem. Res. 2008; 41: 1474
- 4b Knochel P, Millot N, Rodriguez AL, Tucker CE. Preparation and Applications of Functionalized Organozinc Compounds . In Organic Reactions, Vol. 58. Wiley-VCH; Weinheim: 2004: 417
- 4c Knochel P, Leuser H, Cong L.-Z, Perrone S, Kneisel FF. In Handbook of Functionalized Organometallics . Knochel P. Wiley-VCH; Weinheim: 2008: 251-333
- 4d Metal-Catalyzed Cross-Coupling Reactions, 2nd ed. Wiley-VCH; Weinheim: 2008
- 4e Lutter FH, Hofmayer MS, Hammann JM, Malakhov V, Knochel P. Generation and Trapping of Functionalized Aryl- and Heteroarylmagnesium and -Zinc Compounds . In Organic Reactions, Vol. 100. Wiley-VCH; Weinheim: 2019: 63-119
- 5a Krasovskiy A, Malakhov V, Gavryushin A, Knochel P. Angew. Chem. Int. Ed. 2006; 45: 6040 ; Angew. Chem. 2006, 118, 6186
- 5b Benischke AD, Le Corre G, Knochel P. Chem. Eur. J. 2017; 23: 778
- 5c Boudet N, Sase S, Sinha P, Liu C.-Y, Krasovskiy A, Knochel P. J. Am. Chem. Soc. 2007; 129: 12358
- 6a Krasovskiy A, Knochel P. Angew. Chem. Int. Ed. 2004; 43: 3333 ; Angew. Chem. 2004, 116, 3396
- 6b Baron O, Knochel P. Angew. Chem. Int. Ed. 2005; 44: 3133 ; Angew. Chem. 2005, 117, 3193
- 6c Gross S, Heuser S, Ammer C, Heckmann G, Bach T. Synthesis 2011; 199
- 6d Stock C, Höfer F, Bach T. Synlett 2005; 511
- 6e Sämann C, Haag B, Knochel P. Chem. Eur. J. 2012; 18: 16145
- 6f Boudet N, Lachs JR, Knochel P. Org. Lett. 2007; 9: 5525
- 6g Bruña S, Kennedy AR, Fairley M, O’Hara CT. Chem. Eur. J. 2021; 27: 4134
- 7a Desaintjean A, Haupt T, Bole LJ, Judge NR, Hevia E, Knochel P. Angew. Chem. Int. Ed. 2021; 60: 1513 ; Angew. Chem. 2021, 133, 1536
- 7b Bole LJ, Judge NR, Hevia E. Angew. Chem. Int. Ed. 2021; 60: 7626 ; Angew. Chem. 2021, 133, 7704
- 8a Blümke TD, Klatt T, Koszinowski K, Knochel P. Angew. Chem. Int. Ed. 2012; 51: 9926 ; Angew. Chem. 2012, 124, 10064
- 8b Balkenhohl M, Knochel P. Chem. Eur. J. 2020; 26: 3688
- 9 Balkenhohl M, Ziegler DS, Desaintjean A, Bole LJ, Kennedy AR, Hevia E, Knochel P. Angew. Chem. Int. Ed. 2019; 58: 12898 ; Angew. Chem. 2019, 131, 13030
- 10 37% of the corresponding carboxylic acid was obtained after hydrolysis.
- 11 Benischke AD, Anthore-Dalion L, Kohl F, Knochel P. Chem. Eur. J. 2018; 24: 11103
- 12 Krasovskiy A, Knochel P. Synthesis 2006; 890