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Synthesis 2022; 54(09): 2157-2164
DOI: 10.1055/a-1730-2473
DOI: 10.1055/a-1730-2473
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Tuning StackPhim Ligands: Applications in Enantioselective Borylation and Alkynylation
The authors thank the University of Florida and the National Science Foundation (CHE-1900299) for their generous support. Mass spectrometry instrumentation was supported by a grant from the National Institutes of Health (S10 OD021758-01A1).
Abstract
Here we present a new stack ligand with a modified imidazoline backbone prepared from cyclohexanediamine. This new stack ligand, Cy-StackPhim, has been found to complement the parent StackPhim ligand in an enantioselective borylation reaction. Additionally, a correlation between the nature of substituents on the imidazoline ring and the substituents on the electrophile is also discussed.
Key words
axial chirality - stack ligands - P,N-ligands - ligand tuning - borylation - alkynylation - A3-coupling - ligand synthesisSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1730-2473.
- Supporting Information
Publication History
Received: 24 November 2021
Accepted after revision: 03 January 2022
Accepted Manuscript online:
03 January 2022
Article published online:
23 March 2022
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References
- 1 Privileged Chiral Ligands and Catalysts . Zhou Q.-L. Wiley-VCH; Weinheim, Germany: 2011
- 2 Yoon TP, Jacobsen EN. Science 2003; 299: 1691
- 3 Pfaltz A, Drury WJ. Proc. Natl. Acad. Sci. U. S. A. 2004; 101: 5723
- 4 Zhang Z, Qian H, Longmire J, Zhang X. J. Org. Chem. 2000; 65: 6223
- 5 Palucki M, Finney NS, Pospisil PJ, Güler ML, Ishida T, Jacobsen EN. J. Am. Chem. Soc. 1998; 120: 948
- 6 Jensen KH, Sigman MS. J. Org. Chem. 2010; 75: 7194
- 7 Engle KM, Yu JQ. J. Org. Chem. 2013; 78: 8927
- 8 Noyori R, Takaya H. Acc. Chem. Res. 1990; 23: 345
- 9 Berthod M, Mignani G, Woodward G, Lemaire M. Chem. Rev. 2005; 105: 1801
- 10 Jeulin S, De Paule SD, Ratovelomanana-Vidal V, Genêt JP, Champion N, Dellis P. Proc. Natl. Acad. Sci. U. S. A. 2004; 101: 5799
- 11 Cardoso FS. P, Abboud KA, Aponick A. J. Am. Chem. Soc. 2013; 135: 14548
- 12 Pappoppula M, Cardoso FS. P, Garrett BO, Aponick A. Angew. Chem. Int. Ed. 2015; 54: 15202
- 13 Pappoppula M, Aponick A. Angew. Chem. Int. Ed. 2015; 54: 15827
- 14 DeRatt LG, Pappoppula M, Aponick A. Angew. Chem. Int. Ed. 2019; 58: 8416
- 15 Mangadan AR. K, Liu J, Aponick A. Angew. Chem. Int. Ed. 2021; 60: 22224
- 16 Mishra S, Liu J, Aponick A. J. Am. Chem. Soc. 2017; 139: 3352
- 17 Mishra S, Aponick A. Angew. Chem. Int. Ed. 2019; 58: 9485
- 18 Paioti PH. S, Abboud KA, Aponick A. ACS Catal. 2017; 7: 2133
- 19 Rokade BV, Guiry PJ. ACS Catal. 2017; 7: 2334
- 20 Dahiya G, Pappoppula M, Aponick A. Angew. Chem. Int. Ed. 2021; 60: 19604
- 21 Lee J.-E, Yun J. Angew. Chem. Int. Ed. 2008; 47: 145
- 22 Luo Y, Roy ID, Madec AG. E, Lam HW. Angew. Chem. Int. Ed. 2014; 53: 4186
- 23 Chen I.-H, Yin L, Itano W, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2009; 131: 11664
- 24 Feng X, Yun J. Chem. Commun. 2009; 6577
- 25 Miwa Y, Kamimura T, Sato K, Shishido D, Yoshida K. J. Org. Chem. 2019; 84: 14291
- 26 O’Brien JM, Lee K, Hoveyda AH. J. Am. Chem. Soc. 2010; 132: 10630
- 27 Wang L, Chen Z, Ma M, Duan W, Song C, Ma Y. Org. Biomol. Chem. 2015; 13: 10691
- 28 Check CT, Jang KP, Schwamb CB, Wong AS, Wang MH, Scheidt KA. Angew. Chem. Int. Ed. 2015; 54: 4264
- 29 CCDC 2123413 (L5) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures. See the Supporting Information for crystallographic data and experimental details of the structure determination.
- 30 Fleming WJ, Müller-Bunz H, Lillo V, Fernández E, Guiry PJ. Org. Biomol. Chem. 2009; 7: 2520
- 31 Gommermann N, Koradin C, Polborn K, Knochel P. Angew. Chem. Int. Ed. 2003; 42: 5763
- 32 Rokade BV, Barker J, Guiry PJ. Chem. Soc. Rev. 2019; 48: 4766
- 33 Neel AJ, Hilton MJ, Sigman MS, Toste FD. Nature 2017; 543: 637
- 34 Wagner JP, Schreiner PR. Angew. Chem. Int. Ed. 2015; 54: 12274
- 35 Lu G, Liu RY, Yang Y, Fang C, Lambrecht DS, Buchwald SL, Liu P. J. Am. Chem. Soc. 2017; 139: 16548
- 36 Cannon JS, Frederich JH, Overman LE. J. Org. Chem. 2012; 77: 1939
- 37 Shiomi T, Adachi T, Toribatake K, Zhou L, Nishiyama H. Chem. Commun. 2009; 5987
- 38 Wang YC, Hwang JY, Chen YC, Chuang SC, Yan TH. Tetrahedron: Asymmetry 2000; 11: 1797
- 39 Rokade BV, Guiry PJ. J. Org. Chem. 2019; 84: 5763