How Rhodium(I)-Catalyzed Phosphorus(III)-Directed C–H Bond Functionalizations Can Improve the Catalytic Activities of Phosphines

Zhuan Zhang; Natacha Durand; Jean-François Soulé

doi:10.1055/s-0041-1737325

Synlett, Inhaltsverzeichnis

Synlett 2022; 33(08): 705-712
DOI: 10.1055/s-0041-1737325

synpacts

How Rhodium(I)-Catalyzed Phosphorus(III)-Directed C–H Bond Functionalizations Can Improve the Catalytic Activities of Phosphines

Zhuan Zhang

^bGuangxi Key Laboratory of Electrochemical Energy Materials, School of Chemistry and Chemical Engineering, Guangxi University, Nanning, Guangxi 530004, P. R. of China

,

Natacha Durand

^aUniv Rennes, CNRS, UMR6226, F-3500 Rennes, France

,

Jean-François Soulé ∗

^aUniv Rennes, CNRS, UMR6226, F-3500 Rennes, France

› Institutsangaben

Abstract

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Abstract

Trivalent-phosphorus-containing molecules are widely used in fields ranging from catalysis to materials science. Efficient catalytic methods for their modifications, providing straightforward access to novel hybrid structures with superior catalytic activities, are highly desired to facilitate reaction improvement or discovery. We have recently developed new methods for synthesizing polyfunctional phosphines by C–C cross-couplings through rhodium-catalyzed C–H bond activation. These methods use a native P(III) atom as a directing group, and can be used in regioselective late-stage functionalization of phosphine ligands. Interestingly, some of the modified phosphines outperform their parents in Pd-catalyzed cross-coupling reactions.

1 Introduction

2 Early Examples of Transition-Metal-Catalyzed P(III)-Directed C–H Bond Activation/Functionalizations

3 Synthesis of Polyfunctional Biarylphosphines by Late-Stage Alkylation: Application in Carboxylation Reactions

4 Synthesis of Polyfunctional Biarylphosphines by Late-Stage Alkenylation: Application in Amidation Reactions

5 Conclusion

Keywords

phosphines - C–H bond activation - late-stage functionalization - rhodium catalysis - CO₂ fixation - ligands

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Referenzen

References

1a Berrisford DJ, Bolm C, Sharpless KB. Angew. Chem. Int. Ed. 1995; 34: 1059
1b Crabtree RH. The Organometallic Chemistry of the Transition Metals, 5th ed. Wiley; Hoboken: 2009
1c Lindner R, van den Bosch B, Lutz M, Reek JN. H, van der Vlugt JI. Organometallics 2011; 30: 499
1d Surry DS, Buchwald SL. Chem. Sci. 2011; 2: 27
1e Crabtree RH. New J. Chem. 2011; 35: 18
1f Carroll MP, Guiry PJ. Chem. Soc. Rev. 2014; 43: 819
1g Clevenger AL, Stolley RM, Aderibigbe J, Louie J. Chem. Rev. 2020; 120: 6124
1h Collado A, Nelson DJ, Nolan SP. Chem. Rev. 2021; 121: 8559

2a Phosphorus(III) Ligands in Homogeneous Catalysis: Design and Synthesis . Kamer PC. J, van Leeuwen PW. N. M. Wiley; Chichester: 2012
2b Allen DW. In Organophosphorus Chemistry, Vol. 43. Allen DW, Tebby JC, Loakes D. Royal Society of Chemistry; Cambridge: 2014
2c van Leeuwen PW. N. M. In Organophosphorus Chemistry: From Molecules to Applications, Chap. 1 . Iaroshenko V. Wiley-VCH; Weinheim: 2019

3a He J, Hamann LG, Davies HM. L, Beckwith RE. J. Nat. Commun. 2015; 6: 5943
3b Sharma A, Hartwig JF. Nature 2015; 517: 600
3c Kuninobu Y, Sueki S. Synthesis 2015; 47: 3823
3d Durak LJ, Payne JT, Lewis JC. ACS Catal. 2016; 6: 1451
3e Bauer M, Wang W, Lorion MM, Dong C, Ackermann L. Angew. Chem. Int. Ed. 2018; 57: 203

4a Unoh Y, Hashimoto Y, Takeda D, Hirano K, Satoh T, Miura M. Org. Lett. 2013; 15: 3258
4b Gwon D, Lee D, Kim J, Park S, Chang S. Chem. Eur. J. 2014; 20: 12421
4c Unoh Y, Satoh T, Hirano K, Miura M. ACS Catal. 2015; 5: 6634
4d Jang Y.-S, Dieckmann M, Cramer N. Angew. Chem. Int. Ed. 2017; 56: 15088
4e Wang C.-S, Dixneuf PH, Soulé J.-F. ChemCatChem 2017; 9: 3117
4f Zhang Z, Dixneuf PH, Soulé J.-F. Chem. Commun. 2018; 54: 7265

5a Bedford RB, Coles SJ, Hursthouse MB, Limmert ME. Angew. Chem. Int. Ed. 2003; 42: 112
5b Bedford RB, Betham M, Caffyn AJ. M, Charmant JP. H, Lewis-Alleyne LC, Long PD, Polo-Cerón D, Prashar S. Chem. Commun. 2008; 990
5c Yang J.-F, Wang R.-H, Wang Y.-X, Yao W.-W, Liu Q.-S, Ye M. Angew. Chem. Int. Ed. 2016; 55: 14116
5d Homma Y, Fukuda K, Iwasawa N, Takaya J. Chem. Commun. 2020; 56: 10710

6 Oi S, Watanabe S.-i, Fukita S, Inoue Y. Tetrahedron Lett. 2003; 44: 8665

7a Borah AJ, Shi Z. J. Am. Chem. Soc. 2018; 140: 6062
7b Qiu X, Deng H, Zhao Y, Shi Z. Sci. Adv. 2018; 4: eaau6468
7c Qiu X, Wang P, Wang D, Wang M, Yuan Y, Shi Z. Angew. Chem. Int. Ed. 2019; 58: 1504

8 Crabtree RH. Chem. Rev. 2015; 115: 127
9 Shelby Q, Kataoka N, Mann G, Hartwig J. J. Am. Chem. Soc. 2000; 122: 10718

10a Crawford KM, Ramseyer TR, Daley CJ, Clark TB. Angew. Chem. Int. Ed. Engl. 2014; 53: 7589
10b Wright SE, Richardson-Solorzano S, Stewart TN, Miller CD, Morris KC, Daley CJ. A, Clark TB. Angew. Chem. Int. Ed. 2019; 58: 2834

11 Qiu X, Wang M, Zhao Y, Shi Z. Angew. Chem. Int. Ed. 2017; 56: 7233
12 Tortajada A, Juliá-Hernández F, Börjesson M, Moragas T, Martin R. Angew. Chem. Int. Ed. 2018; 57: 15948
13 Correa A, Martín R. J. Am. Chem. Soc. 2009; 131: 15974
14 Shimomaki K, Murata K, Martin R, Iwasawa N. J. Am. Chem. Soc. 2017; 139: 9467
15 Zhang Z, Roisnel T, Dixneuf PH, Soulé J.-F. Angew. Chem. Int. Ed. 2019; 58: 14110

16a Dong K, Sang R, Wei Z, Liu J, Dühren R, Spannenberg A, Jiao H, Neumann H, Jackstell R, Franke R, Beller M. Chem. Sci. 2018; 9: 2510
16b Sang R, Kucmierczyk P, Dong K, Franke R, Neumann H, Jackstell R, Beller M. J. Am. Chem. Soc. 2018; 140: 5217
16c Dong K, Sang R, Liu J, Razzaq R, Franke R, Jackstell R, Beller M. Angew. Chem. Int. Ed. 2017; 56: 6203

17a Drent E, Arnoldy P, Budzelaar PH. M. J. Organomet. Chem. 1993; 455: 247
17b Crawford L, Cole-Hamilton DJ, Drent E, Bühl M. Chem. Eur. J. 2014; 20: 13923
17c Crawford L, Cole-Hamilton DJ, Bühl M. Organometallics 2015; 34: 438

18a Rataboul F, Zapf A, Jackstell R, Harkal S, Riermeier T, Monsees A, Dingerdissen U, Beller M. Chem. Eur. J. 2004; 10: 2983
18b Zapf A, Jackstell R, Rataboul F, Riermeier T, Monsees A, Fuhrmann C, Shaikh N, Dingerdissen U, Beller M. Chem. Commun. 2004; 38
18c Li H, Dong K, Jiao H, Neumann H, Jackstell R, Beller M. Nat. Chem. 2016; 8: 1159

19 So CM, Zhou Z, Lau CP, Kwong FY. Angew. Chem. Int. Ed. 2008; 47: 6402
20 Martin R, Buchwald SL. Acc. Chem. Res. 2008; 41: 1461
21 Shaughnessy KH. Chem. Rev. 2009; 109: 643
22 Wang D, Dong B, Wang Y, Qian J, Zhu J, Zhao Y, Shi Z. Nat. Commun. 2019; 10: 3539

23a Li J.-W, Wang L.-N, Li M, Tang P.-T, Zhang N.-J, Li T, Luo X.-P, Kurmoo M, Liu Y.-J, Zeng M.-H. Org. Lett. 2020; 22: 1331
23b Li M, Tao J.-Y, Wang L.-N, Li J.-W, Liu Y.-J, Zeng M.-H. J. Org. Chem. 2021; 86: 11915

24 Ruiz-Castillo P, Buchwald SL. Chem. Rev. 2016; 116: 12564
25 Ikawa T, Barder TE, Biscoe MR, Buchwald SL. J. Am. Chem. Soc. 2007; 129: 13001
26 Zhang Z, Cordier M, Dixneuf PH, Soulé J.-F. Org. Lett. 2020; 22: 5936
27 Mahmudov KT, Gurbanov AV, Guseinov FI, Guedes da Silva MF. C. Coord. Chem. Rev. 2019; 387: 32