Nickel-Catalyzed sp3 C–H Activation

Colton E. Johnson; Shangyu Li; Ramon Arora; Bijan Mirabi; Mark Lautens

doi:10.1055/s-0042-1751519

Synlett, Inhaltsverzeichnis

Synlett 2024; 35(08): 851-861
DOI: 10.1055/s-0042-1751519

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Special Issue dedicated to Keith Fagnou

Nickel-Catalyzed sp³ C–H Activation

Authors

Colton E. Johnson
Shangyu Li
Ramon Arora
Bijan Mirabi
Mark Lautens ∗

Abstract

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Abstract

Base metal catalyzed C–H activation represents a highly atom economic method to access functionalized molecules. This Account will focus on Ni-catalyzed C–H activation of sp³-hybridized carbon atoms with a particular focus on mechanism, recent applications, challenges, and outlook in this area. This Account will primarily focus on recent mechanistic work from 2017–2023.
1 Base Metal C–H Activation

2 Nickel-Catalyzed sp³ C–H activation

3 Differences between Ni and Pd

4 Mechanistic Considerations

5 Elementary Steps

6 Directed sp³ C–H Activation

7 Choice of Directing Group

8 Primary C–H Activation

9 Secondary C–H Activation

10 Tertiary C–H Activation

11 Conclusion and Outlook

Key words

C–H activation - nickel - catalysis - mechanism - directing group

Volltext

Referenzen

References
1 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 Primers 2021; 1

2a Gandeepan P, Müller T, Zell D, Cera G, Warratz S, Ackermann L. Chem. Rev. 2019; 119: 2192
2b Docherty JH, Lister TM, McArthur G, Findlay MT, Domingo-Legarda P, Kenyon J, Choudhary S, Larrosa I. Chem. Rev. 2023; 123: 7692

3 Hodges RJ, Garnett JL. J. Catal. 1969; 13: 83
4 Goldshleger NF, Tyabin MB, Shilov AE, Shteinman AA. Russ. J. Phys. Chem. 1969; 43: 1222
5 Dyker G. Angew. Chem., Int. Ed. Engl. 1992; 31: 1023
6 Kleiman JP, Dubeck M. J. Am. Chem. Soc. 1963; 85: 1544
7 Shiota H, Ano Y, Aihara Y, Fukumoto Y, Chatani N. J. Am. Chem. Soc. 2011; 133: 14952
8 Aihara Y, Chatani N. J. Am. Chem. Soc. 2014; 136: 898
9 Wu X, Zhao Y, Ge H. J. Am. Chem. Soc. 2014; 136: 1789

10a Altus KM, Love JA. Commun. Chem. 2021; 4: 173
10b Labinger JA, Bercaw JE. Nature 2002; 417: 507

11a Liu B, Romine AM, Rubel CZ, Engle KM, Shi B.-F. Chem. Rev. 2021; 121: 14957
11b Chu JC. K, Rovis T. Angew. Chem. Int. Ed. 2018; 57: 62
11c Khake SM, Chatani N. Trends Chem. 2019; 1: 524
11d Khake SM, Chatani N. Chem 2020; 6: 1056

12 Harry NA, Saranya S, Ujwaldev SM, Anilkumar G. Catal. Sci. Technol. 2019; 9: 1726

13a Daugulis O, Roane J, Tran LD. Acc. Chem. Res. 2015; 48: 1053
13b Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147

14 Scerri E. J. Chem. Educ. 2008; 85: 585

15a Cooper AK, Burton PM, Nelson DJ. Synthesis 2020; 52: 565
15b West MJ, Watson AJ. B. Org. Biomol. Chem. 2019; 17: 5055

16a Gorelsky SI, Lapointe D, Fagnou K. J. Org. Chem. 2012; 77: 658
16b Gorelsky SI, Lapointe D, Fagnou K. J. Am. Chem. Soc. 2008; 130: 10848

17a Labinger JA. Chem. Rev. 2017; 117: 8483
17b Lersch M, Tilset M. Chem. Rev. 2005; 105: 2471

18 Camasso NM, Canty AJ, Ariafard A, Sanford MS. Organometallics 2017; 36: 4382
19 Poli R, Cacelli I. Eur. J. Inorg. Chem. 2005; 2324
20 Bhatt V. In Essentials of Coordination Chemistry, 1^st ed. Academic Press; Cambridge (MA, USA): 2015: 1-269
21 Ting SI, Garakyaraghi S, Taliaferro CM, Shields BJ, Scholes GD, Castellano FN, Doyle AG. J. Am. Chem. Soc. 2020; 142: 5800
22 Milbauer MW, Kampf JW, Sanford MS. J. Am. Chem. Soc. 2022; 144: 21030

23a D’Accriscio F, Borja P, Saffon-Merceron N, Fustier-Boutignon M, Mézailles N, Nebra N. Angew. Chem. Int. Ed. 2017; 56: 12898
23b Canty AJ. Acc. Chem. Res. 1992; 25: 83
23c Stahl SS, Labinger JA, Bercaw JE. J. Am. Chem. Soc. 1996; 118: 5961
23d Meucci EA, Nguyen SN, Camasso NM, Chong E, Ariafard A, Canty AJ, Sanford MS. J. Am. Chem. Soc. 2019; 141: 12872

24a Dimitrov V, Linden A. Angew. Chem. Int. Ed. 2003; 42: 2631
24b Fekl U, Kaminsky W, Goldberg KI. J. Am. Chem. Soc. 2001; 123: 6423

25 Ferrando R, Jellinek J, Johnston RL. Chem. Rev. 2008; 108: 845
26 Batsanov SS. Inorg. Mater. 2001; 37: 871
27 Lin B.-L, Liu L, Fu Y, Luo S.-W, Chen Q, Guo Q.-X. Organometallics 2004; 23: 2114
28 Uddin J, Morales CM, Maynard JH, Landis CR. Organometallics 2006; 25: 5566
29 Simoes JA. M, Beauchamp JL. Chem. Rev. 1990; 90: 629
30 He J, Wasa M, Chan KS. L, Shao Q, Yu J.-Q. Chem. Rev. 2017; 117: 8754
31 Omer HM, Liu P. J. Am. Chem. Soc. 2017; 139: 9909

32a Song W, Lackner S, Ackermann L. Angew. Chem. Int. Ed. 2014; 53: 2477
32b Hachiya H, Hirano K, Satoh T, Miura M. Org. Lett. 2009; 11: 1737
32c Hachiya H, Hirano K, Satoh T, Miura M. ChemCatChem 2010; 2: 1403
32d Wang X, Xie P, Qiu R, Zhu L, Liu T, Li Y, Iwasaki T, Au C.-T, Xu X, Xia Y, Yin S.-F, Kambe N. Chem. Commun. 2017; 53: 8316
32e Ye X, Petersen JL, Shi X. Chem. Commun. 2015; 51: 7863
32f Wu X, Zhao Y, Ge H. Chem. Eur. J. 2014; 20: 9530

33 Singh SK S, Sunoj RB. J. Org. Chem. 2017; 82: 9619
34 Huo J, Fu Y, Tang MJ, Liu P, Dong G. J. Am. Chem. Soc. 2023; 145: 11005

35a Iyanaga M, Aihara Y, Chatani N. J. Org. Chem. 2014; 79: 11933
35b Liu Y.-H, Xia Y.-N, Shi B.-F. Chin. J. Chem. 2020; 38: 635

36 Kim YB, Won J, Lee J, Kim J, Zhou B, Park J.-W, Baik M.-H, Chang S. ACS Catal. 2021; 11: 3067
37 Desai LV, Stowers KJ, Sanford MS. J. Am. Chem. Soc. 2008; 130: 13285

38a Roberts CC, Chong E, Kampf JW, Canty AJ, Ariafard A, Sanford MS. J. Am. Chem. Soc. 2019; 141: 19513
38b Sahni P, Gupta R, Sharma S, Pal AK. Coord. Chem. Rev. 2023; 474: 214849
38c Camasso NM, Sanford MS. Science 2015; 347: 1218

39 Liu J, Johnson SA. Organometallics 2021; 40: 2970
40 Beattie DD, Grunwald AC, Perse T, Schafer LL, Love JA. J. Am. Chem. Soc. 2018; 140: 12602
41 Brookhart M, Green ML. H, Parkin G. Proc. Natl. Acad. Sci. U.S.A. 2007; 104: 6908
42 Piszel PE, Orzolek BJ, Olszewski AK, Rotella ME, Spiewak AM, Kozlowski MC, Weix DJ. J. Am. Chem. Soc. 2023; 145: 8517
43 Lin L, Spasyuk DM, Lalancette RA, Prokopchuk DE. J. Am. Chem. Soc. 2022; 144: 12632
44 Davies DL, Macgregor SA, McMullin CL. Chem. Rev. 2017; 117: 8649
45 Jutzi P, Müller C, Stammler A, Stammler H.-G. Organometallics 2000; 19: 1442

46a Abdur-Rashid K, Fong TP, Greaves B, Gusev DG, Hinman JG, Landau SE, Lough AJ, Morris RH. J. Am. Chem. Soc. 2000; 122: 9155
46b Kaupmees K, Järviste R, Leito I. Chem. Eur. J. 2016; 22: 17445
46c Tshepelevitsh S, Kütt A, Lõkov M, Kaljurand I, Saame J, Heering A, Plieger PG, Vianello R, Leito I. Eur. J. Org. Chem. 2019; 6735

47 Roy P, Bour JR, Kampf JW, Sanford MS. J. Am. Chem. Soc. 2019; 141: 17382
48 Wang C, Zhang L, You J. Org. Lett. 2017; 19: 1690

49a Lin C, Yu W, Yao J, Wang B, Liu Z, Zhang Y. Org. Lett. 2015; 17: 1340
49b Yan S.-Y, Liu Y.-J, Liu B, Liu Y.-H, Zhang Z.-Z, Shi B.-F. Chem. Commun. 2015; 51: 7341

50 Liu Y.-J, Zhang Z.-Z, Yan S.-Y, Liu Y.-H, Shi B.-F. Chem. Commun. 2015; 51: 7899
51 Uemura T, Yamaguchi M, Chatani N. Angew. Chem. Int. Ed. 2016; 55: 3162
52 Lin C, Chen Z, Zhang Y. Org. Lett. 2017; 19: 850
53 Fitzgerald LS, O’Duill ML. Chem. Eur. J. 2021; 27: 8411
54 Corbet M, De Campo F. Angew. Chem. Int. Ed. 2013; 52: 9896
55 Wang Y.-X, Zhang F.-P, Chen H, Li Y, Li J.-F, Ye M. Angew. Chem. Int. Ed. 2022; 61: e202209625

56a Lucas EL, Lam NY. S, Zhuang Z, Chan HS. S, Strassfeld DA, Yu J.-Q. Acc. Chem. Res. 2022; 55: 537
56b Gandeepan P, Ackermann L. Chem 2018; 4: 199