Cp*CoIII-Catalyzed C–H Functionalization and Asymmetric Reactions Using External Chiral Sources

Tatsuhiko Yoshino; Shigeki Matsunaga

doi:10.1055/s-0037-1611814

Synlett, Inhaltsverzeichnis

Synlett 2019; 30(12): 1384-1400
DOI: 10.1055/s-0037-1611814

account

Cp*Co^III-Catalyzed C–H Functionalization and Asymmetric Reactions Using External Chiral Sources

Tatsuhiko Yoshino*

,

Shigeki Matsunaga*

Abstract

Alle Artikel dieser Rubrik

Abstract

This account describes Cp*Co^III-catalyzed C–H functionalization reactions developed in our group between 2013 and 2018. Cp*Co^III catalysts not only serve as inexpensive alternatives to Cp*Rh^III catalysts but also exhibit unique reactivity and selectivity in several transformations. In the latter part of this review, we introduce catalytic asymmetric C–H functionalization reactions using achiral Rh^III or Co^III catalysts with chiral disulfonates or carboxylic acids as external chiral sources.

1 Introduction and Overview

2 Cp*Co^III-Catalyzed C–H Functionalization Reactions

2.1 C–H Addition Reactions to Polar Double Bonds

2.2 Cp*Co(CO)I₂ and [Cp*CoI₂]₂ Precursors for the C2-selective C–H Amidation of Indoles

2.3 C–H Functionalization of Carbamoyl-Protected Indoles Using Alkynes

2.4 C–H Allylation Using Allyl Alcohols

2.5 Cyclization Reactions of O-Acyloximes and Alkynes

2.6 Other Miscellaneous Reactions

3 Enantioselective C–H Functionalization Reactions by Hybrid Catalysis

3.1 Cp*Rh^III/Chiral Disulfonate Catalysts for the Enantioselective C–H Addition to Enones

3.2 Enantioselective C–H Cleavage Using Chiral Carboxylic Acids

4 Summary and Perspective

Key words

C–H functionalization - C–H activation - cobalt - rhodium - asymmetric catalysis

Volltext

Referenzen

References

Selected general reviews on C–H functionalization:

1a Gutekunst WR, Baran PS. Chem. Soc. Rev. 2011; 40: 1976
1b Yamaguchi J, Yamaguchi AD, Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
1c Dong Z, Ren Z, Thompson SJ, Xu Y, Dong G. Chem. Rev. 2017; 117: 9333
1d He J, Wasa M, Chan KS. L, Shao Q, Yu J.-Q. Chem. Rev. 2017; 117: 8754
1e Hummel JR, Boerth JA, Ellman JA. Chem. Rev. 2017; 117: 9163
1f Karimov RR, Hartwig JF. Angew. Chem. Int. Ed. 2018; 57: 4234
1g Sambiagio C, Schönbauer D, Blieck R, Dao-Huy T, Pototschnig G, Schaaf P, Wiesinger T, Zia MF, Wencel-Delord J, Besset T, Maes BU. W, Schnürch M. Chem. Soc. Rev. 2018; 47: 6603
1h Abrams DJ, Provencher PA, Sorensen EJ. Chem. Soc. Rev. 2018; 47: 8925 (i) Rej, S.; Chatani, N. Angew. Chem. Int. Ed. 2018, in press; DOI: 10.1002/anie.201808159

2 Trost BM. Science 1991; 254: 1471
3 Wender PA, Miller BL. Nature 2009; 460: 197

4a Ueura K, Satoh T, Miura M. Org. Lett. 2007; 9: 1407
4b Ueura K, Satoh T, Miura M. J. Org. Chem. 2007; 72: 5362

Reviews on Cp*Rh^III-catalyzed C–H functionalization reactions:

5a Satoh T, Miura M. Chem. Eur. J. 2010; 16: 11212
5b Patureau FW, Wencel-Delord J, Glorius F. Aldrichimica Acta 2012; 45: 31
5c Song G, Wang F, Li X. Chem. Soc. Rev. 2012; 41: 3651
5d Chiba S. Chem. Lett. 2012; 41: 1554
5e Kuhl N, Schröder N, Glorius F. Adv. Synth. Catal. 2014; 356: 1443
5f Song G, Li X. Acc. Chem. Res. 2015; 48: 1007
5g Piou T, Rovis T. Acc. Chem. Res. 2018; 51: 170

6a Kulkarni AA, Daugulis O. Synthesis 2009; 4087
6b Miao J, Ge H. Eur. J. Org. Chem. 2015; 7859
6c Pototschnig G, Maulide N, Schnürch M. Chem. Eur. J. 2017; 23: 9206
6d Rajesh N, Barsu N, Sundararaju B. Tetrahedron Lett. 2018; 59: 862
6e Gandeepan P, Müller T, Zell D, Cera G, Warratz S, Ackermann L. Chem. Rev. 2019; 119: 2192

7a Murahashi S. J. Am. Chem. Soc. 1955; 77: 6403
7b Murahashi S, Horiie S. J. Am. Chem. Soc. 1956; 78: 4816
7c Halbritter G, Knoch F, Wolski A, Kisch H. Angew. Chem., Int. Ed. Engl. 1994; 33: 1603
7d Lenges CP, Brookhart M. J. Am. Chem. Soc. 1997; 119: 3165
7e Bolig AD, Brookhart M. J. Am. Chem. Soc. 2007; 129: 14544

8 Gao K, Lee P.-S, Fujita T, Yoshikai N. J. Am. Chem. Soc. 2010; 132: 12249

General reviews on cobalt-catalyzed C–H functionalization:

9a Gao K, Yoshikai N. Acc. Chem. Res. 2014; 47: 1208
9b Moselage M, Li J, Ackermann L. ACS Catal. 2016; 6: 498
9c Usman M, Ren Z.-H, Wang Y.-Y, Guan Z.-H. Synthesis 2017; 49: 1419
9d Yoshino T, Matsunaga S. Asian J. Org. Chem. 2018; 7: 1193

Several stoichiometric C–H activation reactions with Co^III had been reported as of 2013:

10a Kanamori K, Broderick WE, Jordan RF, Willett RD, Legg JI. J. Am. Chem. Soc. 1986; 108: 7122
10b Broderick WE, Kanamori K, Willett RD, Legg JI. Inorg. Chem. 1991; 30: 3875
10c Avilés T, Dinis A, Calhorda MJ, Pinto P, Félix V, Drew MG. B. J. Organomet. Chem. 2001; 625: 186

11a Grigorjeva L, Daugulis O. Angew. Chem. Int. Ed. 2014; 53: 10209
11b Review: Kommagalla Y, Chatani N. Coord. Chem. Rev. 2017; 350: 117

12a Yoshino T, Matsunaga S. Adv. Synth. Catal. 2017; 359: 1245
12b Wang S, Chen S.-Y, Yu X.-Q. Chem. Commun. 2017; 53: 3165
12c Chirila PG, Whiteoak CJ. Dalton Trans. 2017; 46: 9721
12d Yoshino T, Matsunaga S. Adv. Organomet. Chem. 2017; 68: 197

Reviews on Cp*M^III-catalyzed C–H functionalization reactions:

13a Park J, Chang S. Chem. Asian J. 2018; 13: 1089
13b Peneau A, Guillou C, Chabaud L. Eur. J. Org. Chem. 2018; 5777

Recent reviews on enantioselective C–H functionalization:

14a Newton CG, Wang S.-G, Oliveira CC, Cramer N. Chem. Rev. 2017; 117: 8908
14b Saint-Denis TG, Zhu R.-Y, Chen G, Wu Q.-F, Yu J.-Q. Science 2018; 359: eaao4798

15a Lapointe D, Fagnou K. Chem. Lett. 2010; 39: 1118
15b Ackermann L. Chem. Rev. 2011; 111: 1315
15c Davies DL, Macgregor SA, McMullin CL. Chem. Rev. 2017; 117: 8649

For external CMD, see:

15d Flegeau EF, Bruneau C, Dixneuf PH, Jutand A. J. Am. Chem. Soc. 2011; 133: 10161
15e Jiang J, Ramozzi R, Morokuma K. Chem. Eur. J. 2015; 21: 11158
15f Sen M, Emayavarambanm B, Barsu N, Premkumar JR, Sundararaju B. ACS Catal. 2016; 6: 2792

16a Ye B, Cramer N. Science 2012; 338: 504
16b Ye B, Cramer N. J. Am. Chem. Soc. 2013; 135: 636

17a Hyster TK, Knörr L, Ward TR, Rovis T. Science 2012; 338: 500
17b Zheng J, Cui W.-J, Zheng C, You S.-L. J. Am. Chem. Soc. 2016; 138: 5242
17c Jia Z.-J, Merten C, Gontla R, Daniliuc CG, Antonchick AP, Waldmann H. Angew. Chem. Int. Ed. 2017; 56: 2429
17d Smits G, Audic B, Wodrich MD, Corminboeuf C, Cramer N. Chem. Sci. 2017; 8: 7174
17e Sun Y, Cramer N. Chem. Sci. 2018; 9: 2981
17f Trifonova EA, Ankudinov NM, Mikhaylov AA, Chusov DA, Nelyubina YV, Perekalin DS. Angew. Chem. Int. Ed. 2018; 57: 7714

18a Ye B, Cramer N. Acc. Chem. Res. 2015; 48: 1308
18b Newton CG, Kossler D, Cramer N. J. Am. Chem. Soc. 2016; 138: 3935

19 Yoshino T, Ikemoto H, Matsunaga S, Kanai M. Angew. Chem. Int. Ed. 2013; 52: 2207

For preparation and properties of Cp*Co^III-arene complexes:

20a Fischer EO, Fischer RD. Z. Naturforsch., B: Anorg. Chem., Org. Chem., Biochem., Biophys., Biol. 1961; 16: 556
20b Fairhurst G, White C. J. Chem. Soc., Dalton Trans. 1979; 1531
20c Kölle U, Fuss B, Rajasekharan MV, Ramakrishna BL, Ammeter JH, Böhm MC. J. Am. Chem. Soc. 1984; 106: 4152

21 Yoshino T, Ikemoto H, Matsunaga S, Kanai M. Chem. Eur. J. 2013; 19: 9142
22 Sun B, Yoshino T, Matsunaga S, Kanai M. Adv. Synth. Catal. 2014; 356: 1491
23 Sun B, Yoshino T, Matsunaga S, Kanai M. Chem. Commun. 2015; 51: 4659
24 Fairhurst G, White C. J. Chem. Soc., Dalton Trans. 1979; 1524
25 Frith SA, Spencer J. Inorg. Synth. 1990; 28: 273
26 Ellman and a co-worker reported the synthesis of [Co*Co(C₆H₆)][B(C₆F₅)₄]₂ from [Co*Co(C₆H₆)](PF₆)₂: Hummel JR, Ellman JA. J. Am. Chem. Soc. 2015; 137: 490
27 Ikemoto H, Yoshino T, Sakata K, Matsunaga S, Kanai M. J. Am. Chem. Soc. 2014; 136: 5424
28 Schipper DJ, Hutchinson M, Fagnou K. J. Am. Chem. Soc. 2010; 132: 6910
29 Ikemoto H, Tanaka R, Sakata K, Kanai M, Yoshino T, Matsunaga S. Angew. Chem. Int. Ed. 2017; 56: 7156
30 Sakata K, Eda M, Kitaoka Y, Yoshino T, Matsunaga S. J. Org. Chem. 2017; 82: 7379

For the isolation and structure of alkenyl-Co intermediates, see:

31a Sanjosé-Orduna J, Gallego D, Garcia-Roca A, Martin E, Benet-Buchholz J, Pérez-Temprano MH. Angew. Chem. Int. Ed. 2017; 56: 12137
31b Sen M, Rajesh N, Emayavaramban B, Premkumar JR, Sundararaju B. Chem. Eur. J. 2018; 24: 342

32a Wang H, Schröder N, Glorius F. Angew. Chem. Int. Ed. 2013; 52: 5386
32b Yu S, Li X. Org. Lett. 2014; 16: 1200
32c Feng C, Feng D, Loh T.-P. Chem. Commun. 2015; 51: 342
32d Jo H, Han S, Park J, Choi M, Han SH, Jeong T, Lee S.-Y, Kwak JH, Jung YH, Kim IS. Tetrahedron 2016; 72: 571

For other examples, see a review:

32e Mishra NK, Sharma S, Park J, Han S, Kim IS. ACS Catal. 2017; 7: 2821

33 Shi Z, Boultadakis-Arapinis M, Glorius F. Chem. Commun. 2013; 49: 6489

34a Ho T.-L. Chem. Rev. 1975; 75: 1
34b Woodward S. Tetrahedron 2002; 58: 1017

Early studies on Cp*Co^III-catalyzed C–H allylation reactions using activated allyl alcohols:

35a Yu D.-G, Gensch T, de Azambuja F, Vásquez-Céspedes S, Glorius F. J. Am. Chem. Soc. 2014; 136: 17722
35b Moselage M, Sauermann N, Koeller J, Liu W, Gelman D, Ackermann L. Synlett 2015; 26: 1596
35c A nonactivated allyl alcohol was examined for a C–H allylation reaction using a Cp*Co^III catalyst: Gensch T, Vásquez-Céspedes S, Yu D.-G, Glorius F. Org. Lett. 2015; 17: 3714

36 Suzuki Y, Sun B, Sakata K, Yoshino T, Matsunaga S, Kanai M. Angew. Chem. Int. Ed. 2015; 54: 9944
37 Kalsi D, Laskar RA, Barsu N, Premkumar JR, Sundararaju B. Org. Lett. 2016; 18: 4198
38 Bunno Y, Murakami N, Suzuki Y, Kanai M, Yoshino T, Matsunaga S. Org. Lett. 2016; 18: 2216
39 For an early report on the use of a fluorinated alcohol solvent in Cp*Co^III-catalyzed reactions, see: Sen M, Kalsi D, Sundararaju B. Chem. Eur. J. 2015; 21: 15529
40 Sun B, Yoshino T, Kanai M, Matsunaga S. Angew. Chem. Int. Ed. 2015; 54: 12968
41 For related work, see: Wang H, Koeller J, Liu W, Ackermann L. Chem. Eur. J. 2015; 21: 15525 ; and ref. 39

42a Too PC, Wang Y.-F, Chiba S. Org. Lett. 2010; 12: 5688
42b Too PC, Chua SH, Wong SH, Chiba S. J. Org. Chem. 2011; 76: 6159
42c Zhang X, Chen D, Zhao M, Zhao J, Jia A, Li X. Adv. Synth. Catal. 2011; 353: 719

43 Tanaka R, Ikemoto H, Kanai M, Yoshino T, Matsunaga S. Org. Lett. 2016; 18: 5732
44 Zhang P, Li M, Xue X.-S, Xu C, Zhao Q, Liu Y, Wang H, Guo Y, Lu L, Shen Q. J. Org. Chem. 2016; 81: 7486
45 Yoshida M, Kawai K, Tanaka R, Yoshino T, Matsunaga S. Chem. Commun. 2017; 53: 5974
46 For related work, see: Liu X.-G, Li Q, Wang H. Adv. Synth. Catal. 2017; 359: 1942
47 Murakami N, Yoshida M, Yoshino T, Matsunaga S. Chem. Pharm. Bull. 2018; 66: 51

For early studies on Cp*Co^III-catalyzed C–H/C–F functionalization reactions:

48a Kong L, Zhou X, Li X. Org. Lett. 2016; 18: 6320
48b Zell D, Müller V, Dhawa U, Bursch M, Presa RR, Grimme S, Ackermann L. Chem. Eur. J. 2017; 23: 12145

49a Nahm S, Weinreb SM. Tetrahedron Lett. 1981; 22: 3815
49b Balasubramaniam S, Aidhen IS. Synthesis 2008; 3707
49c Nowak M. Synlett 2015; 26: 561

50 Our group also reported Cp*Co^III-catalyzed oxidative Heck reactions of amides: Suzuki Y, Sun B, Yoshino T, Kanai M, Matsunaga S. Tetrahedron 2015; 71: 4552
51 Kawai K, Bunno Y, Yoshino T, Matsunaga S. Chem. Eur. J. 2018; 24: 10231

Early studies on Cp*Co^III-catalyzed C–H amidation reactions using dioxazolones:

52a Park J, Chang S. Angew. Chem. Int. Ed. 2015; 54: 14103
52b Liang Y, Liang Y.-F, Tang C, Yuan Y, Jiao N. Chem. Eur. J. 2015; 21: 16395

For dioxazolones as amidation reagents, see:

52c Park Y, Park KT, Kim JG, Chang S. J. Am. Chem. Soc. 2015; 137: 4534
52d Park Y, Jee S, Kim JG, Chang S. Org. Process Res. Dev. 2015; 19: 1024 ; and references therein

53 Tanimoto, I. Kawai, K. Sato, A. Yoshino, T.; Matsunaga, S. Heterocycles 2018, in press; DOI: 10.3987/COM-18-S(F)48.

54a Liu H, An Z, He J. ACS Catal. 2014; 4: 3543
54b Gwon D, Park S, Chang S. Tetrahedron 2015; 71: 4504
54c Zell D, Bursch M, Müller V, Grimme S, Ackermann L. Angew. Chem. Int. Ed. 2017; 56: 10378

General reviews on enantioselective metal/organo hybrid catalysis:

55a Shao Z, Zhang H. Chem. Soc. Rev. 2009; 38: 2745
55b Du Z, Shao Z. Chem. Soc. Rev. 2013; 42: 1337
55c Inamdar SM, Shinde VS, Patil NT. Org. Biomol. Chem. 2015; 13: 8116

56a Phipps RJ, Hamilton GL, Toste FD. Nat. Chem. 2012; 4: 603
56b Mahlau M, List B. Angew. Chem. Int. Ed. 2013; 52: 518

57 Mayer S, List B. Angew. Chem. Int. Ed. 2006; 45: 4193
58 Hamilton GL, Kang EJ, Mba M, Toste FD. Science 2007; 317: 496
59 Mukherjee S, List B. J. Am. Chem. Soc. 2007; 129: 11336

For applications of ACDC to Pd-catalyzed C–H functionalization reactions, see:

60a Chai Z, Rainey TJ. J. Am. Chem. Soc. 2012; 134: 3615
60b Wang P.-S, Lin H.-C, Zhai Y.-J, Han Z.-Y, Gong L.-Z. Angew. Chem. Int. Ed. 2014; 53: 12218

61a Pan SC, List B. Chem. Asian J. 2008; 3: 430
61b Hatano M, Maki T, Moriyama K, Arinobe M, Ishihara K. J. Am. Chem. Soc. 2008; 130: 16858

62 Hatano M, Ishihara K. Asian J. Org. Chem. 2014; 3: 352
63 Satake S, Kurihara T, Nishikawa K, Mochizuki T, Hatano M, Ishihara K, Yoshino T, Matsunaga S. Nat. Catal. 2018; 1: 585
64 Pesciaioli F, Dhawa U, Oliveira JC. A, Yin R, John M, Ackermann L. Angew. Chem. Int. Ed. 2018; 57: 15425
65 Kurihara T, Satake S, Hatano M, Ishihara K, Yoshino T, Matsunaga S. Chem. Asian J. 2018; 13: 2378

A pioneering work:

66a Shi B.-F, Maugel N, Zhang Y.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2008; 47: 4882

Selected recent works:

66b Chen G, Gong W, Zhuang Z, Andrä MS, Chen Y.-Q, Hong X, Yang Y.-F, Liu T, Houk KN, Yu J.-Q. Science 2016; 353: 1023
66c He J, Shao Q, Wu Q, Yu J.-Q. J. Am. Chem. Soc. 2017; 139: 3344
66d Plata RE, Hill DE, Haines BE, Musaev DG, Chu L, Hickey DP, Sigman MS, Yu J.-Q, Blackmond DG. J. Am. Chem. Soc. 2017; 139: 9238
66e Wu Q.-F, Shen P.-X, He J, Wang X.-B, Zhang F, Shao Q, Zhu R.-Y, Mapelli C, Qiao JX, Poss MA, Yu J.-Q. Science 2017; 355: 499
66f Shao Q, Wu Q.-F, He J, Yu J.-Q. J. Am. Chem. Soc. 2018; 140: 5322
66g Shen P.-X, Hu L, Shao Q, Hong K, Yu J.-Q. J. Am. Chem. Soc. 2018; 140: 6545 ; for other works, see also ref. 14

67 Yang Y.-F, Hong X, Yu J.-Q, Houk KN. Acc. Chem. Res. 2017; 50: 2853

68a Jang Y.-S, Dieckmann M, Cramer N. Angew. Chem. Int. Ed. 2017; 56: 15088
68b Jang Y.-S, Woźniak Ł, Pedroni J, Cramer N. Angew. Chem. Int. Ed. 2018; 57: 12901
68c Sun Y, Cramer N. Angew. Chem. Int. Ed. 2018; 57: 15539

69 For racemic reactions, see: Chan W.-W, Lo S.-F, Zhou Z, Yu W.-Y. J. Am. Chem. Soc. 2012; 134: 13565
70 Lin L, Fukagawa S, Sekine D, Tomita E, Yoshino T, Matsunaga S. Angew. Chem. Int. Ed. 2018; 57: 12048
71 Fukagawa S, Kato Y, Tanaka R, Kojima M, Yoshino T, Matsunaga S. Angew. Chem. Int. Ed. 2019; 58: 1153

For racemic reactions, see:

72a Tan PW, Mak AM, Sullivan MB, Dixon DJ, Seayad J. Angew. Chem. Int. Ed. 2017; 56: 16550

For related Pd-catalyzed enantioselective C–H functionalization reactions of thioamides, see:

72b Jain P, Verma P, Xia G, Yu J.-Q. Nat. Chem. 2017; 9: 140

For pioneering reports on Cp*Co^III-catalyzed racemic C(sp³)–H functionalization reactions, see:

72c Sen M, Emayavaramban B, Barsu N, Premkumar JR, Sundararaju B. ACS Catal. 2016; 6: 2792
72d Barsu N, Rahman MA, Sen M, Sundararaju B. Chem. Eur. J. 2016; 22: 9135

73 Adly FG, Gardiner MG, Ghanem A. Chem. Eur. J. 2016; 22: 3447
74 Iwata M, Yazaki R, Chen I.-H, Sureshkumar D, Kumagai N, Shibasaki M. J. Am. Chem. Soc. 2011; 133: 5554