Understanding and Describing London Dispersion Effects in ­Transition-Metal-Catalyzed C–H Activations

Binbin Yuan; João C. A. Oliveira; Lutz Ackermann

doi:10.1055/a-2060-3288

Synlett, Table of Contents

Synlett 2023; 34(10): 1098-1112
DOI: 10.1055/a-2060-3288

account

Dispersion Effects

Understanding and Describing London Dispersion Effects in Transition-Metal-Catalyzed C–H Activations

Binbin Yuan‡

^aInstitut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammanstraße 2, 37077 Göttingen, Germany

,

João C. A. Oliveira ‡

^aInstitut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammanstraße 2, 37077 Göttingen, Germany

,

Lutz Ackermann ∗

^aInstitut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammanstraße 2, 37077 Göttingen, Germany

^bWöhler Research Institute for Sustainable Chemistry, Tammanstraße 2, 37077, Göttingen, Germany

› Author Affiliations

Abstract

All articles of this category

Abstract

Transition-metal-catalyzed C–H activation has emerged as a powerful strategy for molecular synthesis with unique levels of resource economy. Weak secondary dispersion interactions were found to play an essential role in these transformations in terms of kinetic efficacy and selectivity. This Account summarizes our group’s recent progress in the rationalization and quantification of London dispersion effects within the transition-metal-catalyzed C–H activation.

1 Introduction

2 Annulation Reactions

3 Alkylation Reactions

4 Arylation Reactions

5 Olefination Reactions

6 Oxygenation Reactions

7 Conclusion

Key words

C–H activation - London dispersion effect - DFT calculations - transition metals - catalysis

Full Text

References

References
1 Gorbachev V, Tsybizova A, Miloglyadova L, Chen P. J. Am. Chem. Soc. 2022; 144: 9007
2 Pace CN, Scholtz JM, Grimsley GR. FEBS Lett. 2014; 588: 2177
3 Hosseini MW. Chem. Commun. 2005; 5825
4 Parveen S, Rana S, Fangueiro R. J. Nanomater. 2013; 710175

5a Gehlhaar A, Schiavo E, Wölper C, Schulte Y, Auer AA, Schulz S. Dalton Trans. 2022; 51: 5016
5b Schiavo E, Bhattacharyya K, Mehring M. Chem. Eur. J. 2021; 27: 14520
5c Fritzsche A.-M, Scholz S, Krasowska M, Bhattacharyya K, Toma AM, Silvestru C, Korb M, Rüffer T, Lang H, Auer AA, Mehring M. Phys. Chem. Chem. Phys. 2020; 22: 10189
5d Krasowska M, Fritzsche A.-M, Mehring M, Auer AA. ChemPhysChem 2019; 20: 2539
5e Preda A.-M, Krasowska ME, Wrobel L, Kitschke P, Andrews PC, MacLellan JG, Mertens L, Korb M, Rüffer T, Lang H, Auer AA, Mehring M. Beilstein J. Org. Chem. 2018; 14: 2125
5f Bistoni G, Auer AA, Neese F. Chem. Eur. J. 2017; 23: 865

6 Berkessel A, Adrio JA. J. Am. Chem. Soc. 2006; 128: 13412
7 Biedermann F, Nau WM, Schneider HJ. Angew. Chem. Int. Ed. 2014; 53: 11158
8 Verevkin S, Kondratev S, Zaitsau D, Zherikova K, Ludwig R. J. Mol. Liq. 2021; 343: 117547

9a Rösel S, Schreiner PR. Isr. J. Chem. 2022; 62: e202200002
9b Wagner JP, Schreiner PR. Angew. Chem. Int. Ed. 2015; 54: 12274

10 Knowles RR, Jacobsen EN. Proc. Natl. Acad. Sci. U.S.A. 2010; 107: 20678

11a Berkessel A, Adrio JA, Hüttenhain D, Neudörfl JM. J. Am. Chem. Soc. 2006; 128: 8421
11b Biedermann F, Nau WM. Angew. Chem. Int. Ed. 2014; 53: 5694

12 Thomas AA, Speck K, Kevlishvili I, Lu Z, Liu P, Buchwald SL. J. Am. Chem. Soc. 2018; 140: 13976

13a Lu Q, Neese F, Bistoni G. Phys. Chem. Chem. Phys. 2019; 21: 11569
13b Lu Q, Neese F, Bistoni G. Angew. Chem. Int. Ed. 2018; 57: 4760
13c Jerhaoui S, Djukic J.-P, Wencel-Delord J, Colobert F. ACS Catal. 2019; 9: 2532
13d Wu F, Deraedt C, Cornaton Y, Contreras-Garcia J, Boucher M, Karmazin L, Bailly C, Djukic J.-P. Organometallics 2020; 39: 2609

14 Detmar E, Mueller V, Zell D, Ackermann L, Breugst M. Beilstein J. Org. Chem. 2018; 14: 1537

15a Li B, Xu H, Dang Y, Houk KN. J. Am. Chem. Soc. 2022; 144: 1971
15b Davies DL, Macgregor SA, McMullin CL. Chem. Rev. 2017; 117: 8649

16 Zell D, Bursch M, Müller V, Grimme S, Ackermann L. Angew. Chem. Int. Ed. 2017; 56: 10378

17a London F. Eur. Phys. J. A 1930; 63: 245
17b London F. Trans. Faraday Soc. 1937; 33: 8b

18a Rummel L, Domanski MH. J, Hausmann H, Becker J, Schreiner PR. Angew. Chem. Int. Ed. 2022; 134: e202204393
18b Solel E, Ruth M, Schreiner PR. J. Am. Chem. Soc. 2021; 143: 20837
18c Maué D, Strebert PH, Bernhard D, Rösel S, Schreiner PR, Gerhards M. Angew. Chem. Int. Ed. 2021; 60: 11305
18d Rösel S, Becker J, Allen WD, Schreiner PR. J. Am. Chem. Soc. 2018; 140: 14421
18e Fokin AA, Zhuk TS, Blomeyer S, Perez C, Chernish LV, Pashenko AE, Antony J, Vishnevskiy YV, Berger RJ. F, Grimme S, Logemann C, Schnell M, Mitzel NW, Schreiner PR. J. Am. Chem. Soc. 2017; 139: 16696
18f Rösel S, Quanz H, Logemann C, Becker J, Mossou E, Delgado LC, Caldeweyher E, Grimme S, Schreiner PR. J. Am. Chem. Soc. 2017; 139: 7428
18g Wagner JP, Schreiner PR. Angew. Chem. Int. Ed. 2015; 54: 12274

19 Löffler S, Wuttke A, Zhang B, Holstein JJ, Mata RA, Clever GH. Chem. Commun. 2017; 53: 11933
20 Grimme S, Hansen A, Brandenburg JG, Bannwarth C. Chem. Rev. 2016; 116: 5105

For selected reviews on C–H activation, see:

21a Rogge T, Kaplaneris N, Chatani N, Kim J, Chang S, Punji B, Schafer LL, Musaev DG, Wencel-Delord J, Roberts CA, Sarpong R, Wilson ZE, Brimble MA, Johansson MJ, Ackermann L. Nat. Rev. Methods Primer 2021; 1: 43
21b Guillemard L, Kaplaneris N, Ackermann L, Johansson M. Nat. Rev. Chem. 2021; 5: 522
21c Wei Y, Hu P, Zhang M, Su W. Chem. Rev. 2017; 117: 8864
21d Leitch JA, Frost CG. Chem. Soc. Rev. 2017; 46: 7145
21e He J, Wasa M, Chan KS. L, Shao Q, Yu J.-Q. Chem. Rev. 2017; 117: 8754
21f Zheng Q.-Z, Jiao N. Chem. Soc. Rev. 2016; 45: 4590
21g Moselage M, Li J, Ackermann L. ACS Catal. 2016; 6: 498
21h Ye B, Cramer N. Acc. Chem. Res. 2015; 48: 1308
21i Wencel-Delord J, Glorius F. Nat. Chem. 2013; 5: 369
21j Rouquet G, Chatani N. Angew. Chem. Int. Ed. 2013; 52: 11726
21k Neufeldt SR, Sanford MS. Acc. Chem. Res. 2012; 45: 936
21l McMurray L, O’Hara F, Gaunt MJ. Chem. Soc. Rev. 2011; 40: 1885
21m Ackermann L, Vicente R, Kapdi AR. Angew. Chem. Int. Ed. 2009; 48: 9792

22a Ikawa T, Yamamoto Y, Heguri A, Fukumoto Y, Murakami T, Takagi A, Masuda Y, Yahata K, Aoyama H, Shigeta Y, Tokiwa H, Akai S. J. Am. Chem. Soc. 2021; 143: 10853
22b Meng G, Lam NY. S, Lucas EL, Saint-Denis TG, Verma P, Chekshin N, Yu J. J. Am. Chem. Soc. 2020; 142: 10571
22c Geiger T, Haupt A, Maichle-Mössmer C, Schrenk C, Schnepf A, Bettinger HF. J. Org. Chem. 2019; 84: 10120
22d Pandit S, Maiti S, Maiti D. Org. Chem. Front. 2021; 8: 4349
22e Bisht R, Hoque ME, Chattopadhyay B. Angew. Chem. Int. Ed. 2018; 57: 15762
22f Hoque ME, Bisht R, Haldar C, Chattopadhyay B. J. Am. Chem. Soc. 2017; 139: 7745
22g Kuninobu Y, Ida H, Nishi M, Kanai M. Nat. Chem. 2015; 7: 712

23a Shen H, Liu T, Cheng D, Yi X, Wang Z, Liu L, Song D, Ling F, Zhong W. J. Org. Chem. 2020; 85: 13735
23b Xu F, Li YJ, Huang C, Xu HC. ACS Catal. 2018; 8: 3820

24a Tian C, Dhawa U, Scheremetjew A, Ackermann L. ACS Catal. 2019; 9: 7690
24b Qiu Y, Stangier M, Meyer TH, Oliveira JC. A, Ackermann L. Angew. Chem. Int. Ed. 2018; 57: 14179
24c Zeng L, Li H, Tang S, Gao X, Deng Y, Zhang G, Pao C.-W, Chen J.-L, Lee J.-F, Lei A. ACS Catal. 2018; 8: 5448
24d Qiu Y, Kong W.-J, Struwe J, Sauermann N, Rogge T, Scheremetjew A, Ackermann L. Angew. Chem. Int. Ed. 2018; 57: 5828

25a Yang L, Steinbock R, Scheremetjew A, Kuniyil R, Finger LH, Messinis AM, Ackermann L. Angew. Chem. Int. Ed. 2020; 59: 11130
25b Yang Q.-L, Xing Y.-K, Wang X.-Y, Ma H.-X, Weng X.-J, Yang X, Guo H.-M, Mei T.-S. J. Am. Chem. Soc. 2019; 141: 18970
25c Kong W.-J, Finger LH, Messinis AM, Kuniyil R, Oliveira JC. A, Ackermann L. J. Am. Chem. Soc. 2019; 141: 17198
25d Mo J, Müller T, Oliveira JC. A, Demeshko S, Meyer F, Ackermann L. Angew. Chem. Int. Ed. 2019; 58: 12874
25e Luo M.-J, Hu M, Song R.-J, He D.-L, Li J.-H. Chem. Commun. 2019; 55: 1124
25f Mei R, Sauermann N, Oliveira JC. A, Ackermann L. J. Am. Chem. Soc. 2018; 140: 7913
25g Mei R, Koeller J, Ackermann L. Chem. Commun. 2018; 54: 12879
25h Tang S, Wang D, Liu Y, Zeng L, Lei A. Nat. Commun. 2018; 9: 798
25i Huang P, Wang P, Wang S, Tang S, Lei A. Green Chem. 2018; 20: 4870
25j Meyer TH, Chandra Sau S, Ang NW. J, Ackermann L. ACS Catal. 2018; 8: 9140

26a Yuan Y, Zhu J, Yang Z, Ni S, Huang Q, Ackermann L. CCS Chem. 2022; 4: 1858
26b Wang Y, Oliveira JC. A, Lin Z, Ackermann L. Angew. Chem. Int. Ed. 2021; 60: 6419

27a Hu P, Kong L, Wang F, Zhu X, Li X. Angew. Chem. Int. Ed. 2021; 60: 2
27b Capdevila L, Meyer TH, Roldán-Gómez S, Luis JM, Ackermann L, Ribas X. ACS Catal. 2019; 9: 11074
27c Kong W.-J, Finger LH, Oliveira JC. A, Ackermann L. Angew. Chem. Int. Ed. 2019; 58: 6342

28a Grimme S, Ehrlich S, Goerigk L. J. Comput. Chem. 2011; 32: 1456
28b Grimme S, Antony J, Ehrlich S, Krieg H. J. Chem. Phys. 2010; 132: 154104

29a Kaplaneris N, Ackermann L. Beilstein J. Org. Chem. 2022; 18: 86
29b Gandeepan P, Finger LH. T, Meyer H, Ackermann L. Chem. Soc. Rev. 2020; 49: 4254
29c Ackermann L. Acc. Chem. Res. 2020; 53: 84
29d Loup J, Dhawa U, Pesciaioli F, Wencel-Delord J, Ackermann L. Angew. Chem. Int. Ed. 2019; 58: 12803
29e Gandeepan P, Müller T, Zell D, Cera G, Warratz S, Ackermann L. Chem. Rev. 2019; 119: 2192

30 Oliveira JC. A, Dhawa U, Ackermann L. ACS Catal. 2021; 11: 1505
31 Liu W, Cera G, Oliveira JC. A, Shen Z, Ackermann L. Chem. Eur. J. 2017; 23: 11524

32a Newton CG, Wang S.-G, Oliveira CC, Cramer N. Chem. Rev. 2017; 117: 8908
32b Borie C, Ackermann L, Nechab M. Chem. Soc. Rev. 2016; 45: 1368

33 Pesciaioli F, Dhawa U, Oliveira JC. A, Yin R, John M, Ackermann L. Angew. Chem. Int. Ed. 2018; 57: 15425
34 Dhawa U, Connon R, Oliveira JC. A, Steinbock R, Ackermann L. Org. Lett. 2021; 23: 2760

35a Choi I, Messinis AM, Ackermann L. Angew. Chem. Int. Ed. 2020; 59: 12534
35b Dias GG, do Nascimento TA, de Almeida AK. A, Bombaça AC. S, Menna-Barreto RF. S, Jacob C, Warratz S, da Silva Júnior EN, Ackermann L. Eur. J. Org. Chem. 2019; 2344
35c Bechtoldt A, Baumert ME, Vaccaro L, Ackermann L. Green Chem. 2018; 20: 398
35d Nareddy P, Jordan F, Szostak M. ACS Catal. 2017; 7: 5721
35e Leitch JA, Frost CG. Chem. Soc. Rev. 2017; 46: 7145
35f Ma W, Gandeepan P, Li J, Ackermann L. Org. Chem. Front. 2017; 4: 1435
35g Zha G.-F, Qin H.-L, Kantchev EA. B. RSC Adv. 2016; 6: 30875

36a Sadowski B, Yuan B, Lin Z, Ackermann L. Angew. Chem. Int. Ed. 2022; 61: e202117188
36b Zhang Y, Struwe J, Ackermann L. Angew. Chem. Int. Ed. 2020; 59: 15076
36c Qiu Y, Scheremetjew A, Ackermann L. J. Am. Chem. Soc. 2019; 141: 2731
36d Qiu Y, Kong W.-J, Struwe J, Sauermann N, Rogge T, Scheremetjew A, Ackermann L. Angew. Chem. Int. Ed. 2018; 57: 5828
36e Piou T, Rovis T. Acc. Chem. Res. 2018; 51: 170
36f Ye B, Cramer N. Acc. Chem. Res. 2015; 48: 1308
36g Song G, Wang F, Li X. Chem. Soc. Rev. 2012; 41: 3651
36h Colby DA, Tsai AS, Bergman RG, Ellman JA. Acc. Chem. Res. 2012; 45: 814
36i Le Bras J, Muzart J. Chem. Rev. 2011; 111: 1170

37a Qiu Y, Stangier M, Meyer TH, Oliveira JC. A, Ackermann L. Angew. Chem. Int. Ed. 2018; 57: 14179
37b Pan S, Shibata T. ACS Catal. 2013; 3: 704
37c Suzuki T. Chem. Rev. 2011; 111: 1825
37d Choi J, Goldman AS. Top. Organomet. Chem. 2011; 34: 139

38a Choy PY, Wong SM, Kapdi A, Kwong FY. Org. Chem. Front. 2018; 5: 288
38b Baudoin O. Acc. Chem. Res. 2017; 50: 1114
38c Ferlin F, Santoro S, Ackermann L, Vaccaro L. Green Chem. 2017; 19: 2510
38d Ma W, Dong H, Wang D, Ackermann L. Adv. Synth. Catal. 2017; 359: 966
38e Della Ca’ N, Fontana M, Motti E, Catellani M. Acc. Chem. Res. 2016; 49: 1389
38f Ye J, Lautens M. Nat. Chem. 2015; 7: 863
38g Neufeldt SR, Sanford MS. Acc. Chem. Res. 2012; 45: 936
38h Sun C.-L, Li B.-J, Shi Z.-J. Chem. Commun. 2010; 46: 677
38i Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
38j Catellani M, Motti E, Della Ca’ N. Acc. Chem. Res. 2008; 41: 1512

39 Meyer TH, Liu W, Feldt M, Wuttke A, Mata RA. Ackermann L. Chem. Eur. J. 2017; 23: 5443
40 Dhawa U, Tian C, Wdowik T, Oliveira JC. A, Hao J, Ackermann L. Angew. Chem. Int. Ed. 2020; 59: 13451
41 Jacob N, Zaid Y, Oliveira JC. A, Ackermann L, Wencel-Delord J. J. Am. Chem. Soc. 2022; 144: 798

42a Zhu C, Oliveira JC. A, Shen Z, Huang H, Ackermann L. ACS Catal. 2018; 8: 4402
42b Ackermann L, Vicente R, Kapdi AR. Angew. Chem. Int. Ed. 2009; 48: 9792
42c Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174

43a Contreras-García J, Johnson ER, Keinan S, Chaudret R, Piquemal J.-P, Beratan DN, Yang W. J. Chem. Theory Comput. 2011; 7: 625
43b Johnson ER, Keinan S, Mori-Sánchez P, Contreras-García J, Cohen AJ, Yang W. J. Am. Chem. Soc. 2010; 132: 6498

44a Jin S, Kim J, Kim D, Park J, Chang S. ACS Catal. 2021; 11: 6590
44b Kim J, Jin S, Kim D, Chang S. Bull. Kor. Chem. Soc. 2021; 42: 529
44c Kim Y, Kim D, Chang S. Chem. Commun. 2021; 57: 12309
44d Kim J, Shin K, Jin S, Kim D, Chang S. J. Am. Chem. Soc. 2019; 141: 4137
44e Shin K, Park Y, Baik M, Chang S. Nat. Chem. 2018; 10: 218

45 Li L, Brennessel WW, Jones WD. J. Am. Chem. Soc. 2008; 130: 12414
46 Wu Z, Su F, Lin W, Song J, Wen T, Zhang H, Xu H. Angew. Chem. Int. Ed. 2019; 58: 1
47 Stangier M, Messinis A, Oliveira JC. A, Yu H, Ackermann L. Nat. Commun. 2021; 12: 4736

48a Ozols K, Jang Y.-S, Cramer N. J. Am. Chem. Soc. 2019; 141: 5675
48b Fukagawa S, Kato Y, Tanaka R, Kojima M, Yoshino T, Matsunaga S. Angew. Chem. Int. Ed. 2019; 58: 1153
48c Pesciaioli F, Dhawa U, Oliveira JC. A, Yin R, John M, Ackermann L. Angew. Chem. Int. Ed. 2018; 57: 1542
48d Zhang L.-B, Hao X.-Q, Liu Z.-J, Zheng X.-X, Zhang S.-K, Niu J.-L, Song M.-P. Angew. Chem. Int. Ed. 2015; 54: 10012
48e Ma W, Ackermann L. ACS Catal. 2015; 5: 2822
48f Grigorjeva L, Daugulis O. Org. Lett. 2015; 17: 1204
48g Grigorjeva L, Daugulis O. Angew. Chem. Int. Ed. 2014; 53: 10209

49 Meyer TH, Oliveira JC. A, Ghorai D, Ackermann L. Angew. Chem. Int. Ed. 2020; 59: 10955

Understanding and Describing London Dispersion Effects in ­Transition-Metal-Catalyzed C–H Activations

Understanding and Describing London Dispersion Effects in Transition-Metal-Catalyzed C–H Activations