Recent Advances in Palladium-Catalyzed C(sp3)–H Activation for the Formation of Carbon–Carbon and Carbon–Heteroatom Bonds

Navid Dastbaravardeh; Maria Christakakou; Maximilian Haider; Michael Schnürch

doi:10.1055/s-0033-1338625

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(11): 1421-1439
DOI: 10.1055/s-0033-1338625

review

Recent Advances in Palladium-Catalyzed C(sp³)–H Activation for the Formation of Carbon–Carbon and Carbon–Heteroatom Bonds

Navid Dastbaravardeh

Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163-OC, 1060 Vienna, Austria Fax: +43(1)588019163616 eMail: michael.schnuerch@tuwien.ac.at

,

Maria Christakakou

Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163-OC, 1060 Vienna, Austria Fax: +43(1)588019163616 eMail: michael.schnuerch@tuwien.ac.at

,

Maximilian Haider

Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163-OC, 1060 Vienna, Austria Fax: +43(1)588019163616 eMail: michael.schnuerch@tuwien.ac.at

,

Michael Schnürch*

Institute of Applied Synthetic Chemistry, Vienna University of Technology, Getreidemarkt 9/163-OC, 1060 Vienna, Austria Fax: +43(1)588019163616 eMail: michael.schnuerch@tuwien.ac.at

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

Within this review, recent developments in the field of C(sp³)–H activation catalyzed by palladium are discussed. Both intra- and intermolecular reactions towards carbon–carbon and carbon–heteroatom bonds are covered. In the case of intramolecular reactions, asymmetric versions are reported as well. The main focus of this review is literature of the last five years until late 2013.

1 Introduction

2 Intramolecular C(sp³)–H Activation

2.1 Carbon–Carbon Coupling

2.2 Carbon–Heteroatom Coupling

2.3 Stereoselective Reactions

3 Intermolecular C(sp³)–H Activation

3.1 Carbon–Carbon Coupling

3.2 Carbon–Heteroatom Coupling

4 Conclusion and Outlook

Key words

alkylation - arylation - palladacycles - homogeneous catalysis - organometallic reagents

Volltext

Referenzen

References

For recent reviews on various aspects of C–H activation, see:

1a Roquet G, Chatani N. Angew. Chem. Int. Ed. 2013; 52: 11726
1b Peng B, Maulide N. Chem. Eur. J. 2013; 19: 13274
1c Thirunavukkarasu VS, Kozhushkov SI, Ackermann L. Chem. Commun. 2014; 50: 29
1d Patureau FW, Wencel-Delord J, Glorius F. Aldrichimica Acta 2012; 45: 31
1e Arockiam PB, Bruneau C, Dixneuf PH. Chem. Rev. 2012; 112: 5879
1f Wencel-Delord J, Glorius F. Nature Chem. 2013; 5: 369

For reviews dedicated to sp² C–H activation, see:

2a Li B, Dixneuf PH. Chem. Soc. Rev. 2013; 42: 5744
2b Engle KM, Yu J.-Q. J. Org. Chem. 2013; 78: 8927
2c Kozhushkov SI, Ackermann L. Chem. Sci. 2013; 4: 886
2d Mousseau JJ, Charette AB. Acc. Chem. Res. 2012; 46: 412
2e Neufeldt SR, Sanford MS. Acc. Chem. Res. 2012; 45: 936

For reviews on sp³ C–H activation, see:

3a Daugulis O, Do H.-Q, Shabashov D. Acc. Chem. Res. 2009; 42: 1074
3b Ramirez TA, Zhao B, Shi Y. Chem. Soc. Rev. 2012; 41: 931
3c Zhang S.-Y, Zhang F.-M, Tu Y.-Q. Chem. Soc. Rev. 2011; 40: 1937
3d Mei T.-S, Kou L, Ma S, Engle KM, Yu J.-Q. Synthesis 2012; 44: 1778

4 Li H, Li B.-J, Shi Z.-J. Catal. Sci. Technol. 2011; 1: 191
5 Dyker G. Angew. Chem. Int. Ed. 1992; 31: 1023
6 Dyker G. Angew. Chem. Int. Ed. 1994; 33: 103
7 Baudoin O, Herrbach A, Gueritte F. Angew. Chem. Int. Ed. 2003; 42: 5736
8 Lafrance M, Gorelsky SI, Fagnou K. J. Am. Chem. Soc. 2007; 129: 14570
9 Watanabe T, Oishi S, Fujii N, Ohno H. Org. Lett. 2008; 10: 1759
10 Liegault B, Fagnou K. Organometallics 2008; 27: 4841
11 Rousseaux S, Gorelsky SI, Chung BK. W, Fagnou K. J. Am. Chem. Soc. 2010; 132: 10692
12 Liang Y, Geng W, Wei J, Ouyang K, Xi Z. Org. Biomol. Chem. 2012; 10: 1537
13 Hsiao C.-C, Lin Y.-K, Liu C.-J, Wu T.-C, Wu Y.-T. Adv. Synth. Catal. 2010; 352: 3267
14 Pierre C, Baudoin O. Org. Lett. 2011; 13: 1816
15 Guyonnet M, Baudoin O. Org. Lett. 2012; 14: 398
16 Sofack-Kreutzer J, Martin N, Renaudat A, Jazzar R, Baudoin O. Angew. Chem. Int. Ed. 2012; 51: 10399
17 Rousseaux S, Liegault B, Fagnou K. Chem. Sci. 2012; 3: 244
18 Saget T, Perez D, Cramer N. Org. Lett. 2013; 15: 1354
19 Ladd CL, Sustac Roman D, Charette AB. Org. Lett. 2013; 15: 1350
20 Feng Y, Wang Y, Landgraf B, Liu S, Chen G. Org. Lett. 2010; 12: 3414
21 Shi Z, Suri M, Glorius F. Angew. Chem. Int. Ed. 2013; 52: 4892
22 Tsukano C, Okuno M, Takemoto Y. Angew. Chem. Int. Ed. 2012; 51: 2763
23 Zhang Q, Yu H.-Z, Fu Y. Organometallics 2013; 32: 4165
24 Tsukano C, Okuno M, Takemoto Y. Chem. Lett. 2013; 42: 753
25 Nanjo T, Tsukano C, Takemoto Y. Org. Lett. 2012; 14: 4270
26 Piou T, Neuville L, Zhu J. Angew. Chem. Int. Ed. 2012; 51: 11561

27a Jones WD. Acc. Chem. Res. 2003; 36: 140
27b Dastbaravardeh N, Kirchner K, Schnürch M, Mihovilovic MD. J. Org. Chem. 2013; 78: 658

28 Simmons EM, Hartwig JF. Angew. Chem. Int. Ed. 2012; 51: 3066
29 Piou T, Bunescu A, Wang Q, Neuville L, Zhu J. Angew. Chem. Int. Ed. 2013; 52: 12385
30 Dong C.-G, Hu Q.-S. Angew. Chem. Int. Ed. 2006; 45: 2289
31 Liu T.-P, Xing C.-H, Hu Q.-S. Angew. Chem. Int. Ed. 2010; 49: 2909
32 Dong C.-G, Hu Q.-S. Tetrahedron 2008; 64: 2537
33 Xie H, Zhang H, Lin Z. New J. Chem. 2013; 37: 2856
34 Ren H, Li Z, Knochel P. Chem. Asian J. 2007; 2: 416
35 Neumann JJ, Rakshit S, Droege T, Glorius F. Angew. Chem. Int. Ed. 2009; 48: 6892
36 He G, Zhao Y, Zhang S, Lu C, Chen G. J. Am. Chem. Soc. 2012; 134: 3
37 Novak P, Correa A, Gallardo-Donaire J, Martin R. Angew. Chem. Int. Ed. 2011; 50: 12236
38 Hartwig JF. Inorg. Chem. 2007; 46: 1936
39 Eom D, Jeong Y, Kim YR, Lee E, Choi W, Lee PH. Org. Lett. 2013; 15: 5210
40 Kündig EP, Seidel TM, Jia Y.-x, Bernardinelli G. Angew. Chem. Int. Ed. 2007; 46: 8484
41 Nakanishi M, Katayev D, Besnard C, Kündig EP. Angew. Chem. Int. Ed. 2011; 50: 7438
42 Larionov E, Nakanishi M, Katayev D, Besnard C, Kündig EP. Chem. Sci. 2013; 4: 1995
43 Anas S, Cordi A, Kagan HB. Chem. Commun. 2011; 47: 11483
44 Martin N, Pierre C, Davi M, Jazzar R, Baudoin O. Chem. Eur. J. 2012; 18: 4480
45 Saget T, Lemouzy SJ, Cramer N. Angew. Chem. Int. Ed. 2012; 51: 2238
46 Saget T, Cramer N. Angew. Chem. Int. Ed. 2012; 51: 12842
47 Zaitsev VG, Shabashov D, Daugulis O. J. Am. Chem. Soc. 2005; 127: 13154

48a Daugulis O, Zaitsev VG. Angew. Chem. Int. Ed. 2005; 44: 4046
48b Shabashov D, Daugulis O. Org. Lett. 2005; 7: 3657

49 Shabashov D, Daugulis O. J. Am. Chem. Soc. 2010; 132: 3965
50 Pan F, Shen P.-X, Zhang L.-S, Wang X, Shi Z.-J. Org. Lett. 2013; 15: 4758
51 Chen K, Hu F, Zhang S.-Q, Shi B.-F. Chem. Sci. 2013; 4: 3906

For examples, see:

52a Matsumura D, Kitazawa K, Terai S, Kochi T, Ie Y, Nitani M, Aso Y, Kakiuchi F. Org. Lett. 2012; 14: 3882
52b Martinez R, Simon M.-O, Chevalier R, Pautigny C, Genêt J.-P, Darses S. J. Am. Chem. Soc. 2009; 131: 7887
52c Preston AJ, Hofacker AL, Parquette JR. Chemtracts 2002; 15: 623
52d Lim Y.-G, Kang J.-B, Kim YH. J. Chem. Soc., Perkin Trans. 1 1996; 17: 2201

53 Zheng B, Jia T, Walsh PJ. Org. Lett. 2013; 15: 4190

54a Lee HW, Lam FL, So CM, Lau CP, Chan AS. C, Kwong FY. Angew. Chem. Int. Ed. 2009; 48: 7436
54b So CM, Lau CP, Kwong FY. Org. Lett. 2007; 9: 2795

55 Xie P, Xia C, Huang H. Org. Lett. 2013; 15: 3370
56 Xie P, Xie Y, Qian B, Zhou H, Xia C, Huang H. J. Am. Chem. Soc. 2012; 134: 9902

57a Jana KJ, Grimme S, Studer A. Chem. Eur. J. 2009; 15: 9078
57b Prokopcova H, Bergman SD, Aelvoet K, Smout V, Herrebout W, Van der Veken B, Meerpoel L, Maes BU. W. Chem. Eur. J. 2010; 16: 13063
57c Smout V, Peschiulli A, Verbeeck S, Herrebout W, Bultinck P, Vande Velde CM. L, Berthelot D, Meerpoel L, Maes BU. W. J. Org. Chem. 2013; 78: 9803
57d Dastbaravardeh N, Schnürch M, Mihovilovic MD. Org. Lett. 2012; 14: 1930

58 Giri R, Maugel N, Li J.-J, Wang D.-H, Breazzano SP, Saunders LB, Yu J.-Q. J. Am. Chem. Soc. 2007; 129: 3510
59 Chen X, Goodhue CE, Yu J.-Q. J. Am. Chem. Soc. 2006; 128: 12634
60 Wang D.-H, Wasa M, Giri R, Yu J.-Q. J. Am. Chem. Soc. 2008; 130: 7190
61 Wasa M, Engle KM, Yu J.-Q. J. Am. Chem. Soc. 2009; 131: 9886
62 Figg TM, Wasa M, Yu J.-Q, Musaev DG. J. Am. Chem. Soc. 2013; 135: 14206
63 Wasa M, Chan KS. L, Zhang X.-G, He J, Miura M, Yu J.-Q. J. Am. Chem. Soc. 2012; 134: 18570
64 He J, Wasa M, Chan KS. L, Yu J.-Q. J. Am. Chem. Soc. 2013; 135: 3387
65 Parella R, Gopalakrishnan B, Babu SA. Org. Lett. 2013; 15: 3238
66 Zhang J, Bellomo A, Creamer AD, Dreher SD, Walsh PJ. J. Am. Chem. Soc. 2012; 134: 13765

67a Dreher SD, Dormer PG, Sandrock DL, Molander GA. J. Am. Chem. Soc. 2008; 130: 9257
67b Dreher SD, Lim SE, Sandrock DL, Molander GA. J. Org. Chem. 2009; 74: 3626
67c Molander GA, Argintaru OA, Aron I, Dreher SD. Org. Lett. 2010; 12: 5783
67d Molander GA, Trice SL. J, Dreher SD. J. Am. Chem. Soc. 2010; 132: 17701
67e Sandrock DL, Jean-Gerard L, Chen CY, Dreher SD, Molander GA. J. Am. Chem. Soc. 2010; 132: 17108

68 Wang G.-W, Zhou A.-X, Wang J.-J, Hu R.-B, Yang S.-D. Org. Lett. 2013; 15: 5270

69a Baumann M, Baxendale IR, Ley SV, Nikbin N. Beilstein J. Org. Chem. 2011; 7: 442
69b Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry and Biochemistry and the Role of Heterocycles in Science, Technology, Medicine, and Agriculture. Pozharsky AF, Soldatenkov AT, Katritzky AR. John Wiley and Sons; Chichester: 1997
69c Bellus D. Lect. Heterocycl. Chem. 1987; 9: 65
69d Muller T, Braese S. Angew. Chem. Int. Ed. 2011; 50: 11844
69e Rasmussen SC, Schwiderski RL, Mulholland ME. Chem. Commun. 2011; 47: 11394
69f Maly KE. J. Mat. Chem. 2009; 19: 1781
69g Elbing M, Bazan GC. Angew. Chem. Int. Ed. 2008; 47: 834

70 Thu H.-Y, Yu W.-Y, Che C.-M. J. Am. Chem. Soc. 2006; 128: 9048
71 Stowers KJ, Kubota A, Sanford MS. Chem. Sci. 2012; 3: 3192
72 Ren Z, Mo F, Dong G. J. Am. Chem. Soc. 2012; 134: 16991
73 Kubota A, Sanford MS. Synthesis 2011; 2579
74 Zhao D, Zhu M.-X, Wang Y, Shen Q, Li J.-X. Org. Biomol. Chem. 2013; 11: 6246
75 Iglesias A, Álvarez R, de Lera AR, Muñiz K. Angew. Chem. Int. Ed. 2012; 51: 2225
76 Baudoux J, Cahard D. Org. React. (N. Y.) 2007; 69: 347
77 Wang D.-H, Hao X.-S, Wu D.-F, Yu J.-Q. Org. Lett. 2006; 8: 3387
78 Kuhl N, Hopkinson MN, Wencel-Delord J, Glorius F. Angew. Chem. Int. Ed. 2012; 51: 10236