Carbonylated Indoles from PdII-Catalyzed Intermolecular Reactions of Indolyl Cores

Jean Le Bras; Jacques Muzart

doi:10.1055/s-0037-1611478

Synthesis, Table of Contents

Synthesis 2019; 51(15): 2871-2890
DOI: 10.1055/s-0037-1611478

review

Carbonylated Indoles from Pd^II-Catalyzed Intermolecular Reactions of Indolyl Cores

Jean Le Bras

,

Jacques Muzart*

Institut de Chimie Moléculaire de Reims, UMR 7312, CNRS - Université de Reims Champagne-Ardenne, B.P. 1039, 51687 Reims Cedex 2, France Email: jacques.muzart@univ-reims.fr

› Author Affiliations

Abstract

All articles of this category

Abstract

This review summarizes palladium-catalyzed carbonylation, transmetalation, and cross-coupling reactions that lead to carbonylated indoles from indoles and indolyl compounds. Special attention is drawn to procedures involving the C(sp²)–H substitution of free (NH)-indoles or (N-substituted)-indoles. Proposed mechanisms are described with, in some cases, personal comments.

1 Introduction

2 Carbonylative Reactions

2.1 Indolyl Halides as Starting Substrates

2.2 Indolyl Iodides as Intermediates

2.3 Indolylborates as Intermediates

2.4 C(sp²)–H Reactions

2.4.1 Carboxylation

2.4.2 Carbonylative Alkoxylation

2.4.3 Carbonylative Arylation

2.4.4 Carbonylative Alkenylation

2.4.5 Carbonylative Alkylation

2.4.6 Double Carbonylation

3 Cross-Coupling of Stannyl- or Mercurioindoles

4 Cross-Coupling of Indoles

4.1 Aldehydes

4.2 Alcohols

4.3 α-Diketones

4.4 α-Oxo Esters

4.5 α-Oxocarboxylic Acids

4.6 Nitriles

4.7 Isocyanides

4.8 Isothiocyanates and Isocyanates

4.9 α-Aminocarbonyl Compounds

4.10 Vinyl Ethers or Vinyl Amides

4.11 Toluene and Substituted Toluenes

4.12 Bromodichloromethane

5 Conclusion

Key words

acylation - carbonylation - palladium - catalysis - indoles

Full Text

References

References

1a Bandini M, Melloni A, Tommasi S, Umani-Ronchi A. Synlett 2005; 1199
1b Joucla L, Djakovitch L. Adv. Synth. Catal. 2009; 351: 673
1c Bandini M, Eichholzer A. Angew. Chem. Int. Ed. 2009; 48: 9608
1d Bartoli G, Bencivenni G, Dalpozzo R. Chem. Soc. Rev. 2010; 39: 4449
1e Shiri M. Chem. Rev. 2012; 112: 3508
1f Lancianesi S, Palmieri A, Petrini M. Chem. Rev. 2014; 114: 7108
1g Dalpozzo R. Chem. Soc. Rev. 2015; 44: 742
1h Petrini M. Chem. Eur. J. 2017; 23: 16115
1i Ziarani GM, Moradi R, Ahmadi T, Lashgari N. RSC Adv. 2018; 8: 12069
1j Pirovano V. Eur. J. Org. Chem. 2018; 1925
1k Ieronimo G, Palmisano G, Maspero A, Marzorati A, Scapinello L, Masciocchi N, Cravotto G, Barge A, Simonetti M, Ameta KL, Nicholas KM, Penoni A. Org. Biomol. Chem. 2018; 16: 6853

2a Norman MH, Navas FIII, Thompson JB, Rigdon GC. J. Med. Chem. 1996; 39: 4692
2b Thurmond RL, Desai PJ, Dunford PJ, Fung-Leung W.-P, Hofstra CL, Jiang W, Nguyen S, Riley JP, Sun S, Williams KN, Edwards JP, Karlsson L. J. Pharmacol. Exp. Ther. 2004; 309: 404
2c Pedras MS. C, Yaya EE, Glawischnig E. Nat. Prod. Rep. 2011; 28: 1381
2d Sravanthi TV, Manju SL. Eur. J. Pharm. Sci. 2016; 91: 1
2e Chadha N, Silakari O. Eur. J. Med. Chem. 2017; 134: 159
2f Ciulla MG, Kumar K. Tetrahedron Lett. 2018; 59: 3223

3a Cacchi S, Fabrizi G. Chem. Rev. 2005; 105: 2873
3b Lang R, Xia C, Li F. New J. Chem. 2014; 38: 2732
3c Wu X.-F. Chem. Eur. J. 2015; 21: 12252
3d Yao S.-J, Ren Z.-H, Guan Z.-H. Tetrahedron Lett. 2016; 57: 3892
3e Sharma S, Mishra NK, Shin Y, Kim IS. Curr. Org. Chem. 2016; 20: 471
3f Wei Y, Hu P, Zhang M, Su W. Chem. Rev. 2017; 117: 8864
3g Hummel JR, Boerth JA, Ellman JA. Chem. Rev. 2017; 117: 9163
3h Wegmann M, Henkel M, Bach T. Org. Biomol. Chem. 2018; 16: 5376
3i Shah TA, De P B, Pradhan S, Punniyamurthy T. Chem. Commun. 2019; 55: 572

4 Grimster NP, Gauntlett C, Godfrey CR. A, Gaunt MJ. Angew. Chem. Int. Ed. 2005; 44: 3185
5 Stuart DR, Villemure E, Fagnou K. J. Am. Chem. Soc. 2007; 129: 12072
6 Joucla L, Batail N, Djakovitch L. Adv. Synth. Catal. 2010; 352: 2929
7 Pi J.-J, Lu X.-Y, Liu J.-H, Lu X, Xiao B, Fu Y, Guimond N. J. Org. Chem. 2018; 83: 5791
8 Moncea O, Poinsot D, Fokin AA, Schreiner PR, Hierso J.-C. ChemCatChem 2018; 10: 2915
9 Potavathri S, Pereira KC, Gorelsky SI, Pike A, LeBris AP, DeBoef B. J. Am. Chem. Soc. 2010; 132: 14676
10 Li Y, Wang W.-H, He K.-H, Shi Z.-J. Organometallics 2012; 31: 4397
11 Tokuyama H, Kaburagi Y, Chen X, Fukuyama T. Synthesis 2000; 429
12 Zhao M.-N, Ran L, Chen M, Ren Z.-H, Wang Y.-Y, Guan Z.-H. ACS Catal. 2015; 5: 1210
13 Karpov AS, Merkul E, Rominger F, Müller TJ. J. Angew. Chem. Int. Ed. 2005; 44: 6951
14 Herbert JM, McNeill AH. Tetrahedron Lett. 1998; 39: 2421
15 Buscemi G, Miller PW, Kealey S, Gee AD, Long NJ, Passchier J, Vilar R. Org. Biomol. Chem. 2011; 9: 3499
16 Kumar K, Zapf A, Michalik D, Tillack A, Heinrich T, Böttcher H, Arlt M, Beller M. Org. Lett. 2004; 6: 7
17 Takács A, Marosvölgyi-Haskó D, Kabak-Solt Z, Damas L, Rodrigues FM. S, Carrilho RM. B, Pineiro M, Pereira MM, Kollár L. Tetrahedron 2016; 72: 247
18 Do H.-Q, Daugulis O. J. Am. Chem. Soc. 2011; 133: 13577
19 Lang R, Shi L, Li D, Xia CG, Li FW. Org. Lett. 2012; 14: 4130
20 Li D, Shan S, Shi L, Lang R, Xia CG, Li FW. Chin. J. Catal. 2013; 34: 185
21 Xing Q, Shi L, Lang R, Xia CG, Li FW. Chem. Commun. 2012; 48: 11023
22 Tu D, Luo J, Jiang C. Chem. Commun. 2018; 54: 2514
23 Ishikura M, Terashima M. J. Org. Chem. 1994; 59: 2634
24 Ishikura M, Imaizumi K, Katagiri N. Heterocycles 2000; 53: 2201
25 Ishikura M, Uchiyama H, Matsuzaki N. Heterocycles 2001; 55: 1063
26 Ishikura M, Matsuzaki Y, Agata I. Chem. Commun. 1996; 2409
27 Itahara T. Chem. Lett. 1982; 1151
28 Lang R, Wu J, Shi L, Xia C, Li F. Chem. Commun. 2011; 47: 12553
29 Zhang H, Liu D, Chen C, Liu C, Lei A. Chem. Eur. J. 2011; 17: 9581

30a Larock RC, Hightower TR. J. Org. Chem. 1993; 58: 5298
30b Muzart J. In Comprehensive Organic Synthesis, 2nd ed., Vol. 7. Molander GA, Knochel P. Elsevier; Oxford: 2014: 295-301

31 Tjutrins J, Arndtsen BA. J. Am. Chem. Soc. 2015; 137: 12050
32 Bis(indolyl)arylmethanes have been obtained using formic acid as CO source: Qi X, Ai H.-J, Zhang N, Peng J.-B, Ying J, Wu X.-F. J. Catal. 2018; 362: 74
33 Nadres ET, Lazareva A, Daugulis O. J. Org. Chem. 2011; 76: 471
34 Liégault B, Petrov I, Gorelsky SI, Fagnou K. J. Org. Chem. 2010; 75: 1047
35 Liu J, Wei Z, Jiao H, Jackstell R, Beller M. ACS Cent. Sci. 2018; 4: 30
36 Ketcha DM, Gribble GW. J. Org. Chem. 1985; 50: 5451
37 Zeng F, Alper H. Org. Lett. 2013; 15: 2034
38 The positive charge of intermediate ²¹D is missing in the original paper.
39 For the formation of η³-allyl palladium complexes from allyl alcohols and their reactivity, see: Muzart J. Tetrahedron 2005; 61: 4179

40a Kimura M, Futamata M, Mukai R, Tamaru Y. J. Am. Chem. Soc. 2005; 127: 4592
40b Tseng Y.-L, Liang M.-C, Chen I.-C, Wu Y.-K. Synlett 2018; 29: 609

41 Wang Z, Yin Z, Wu X.-F. Chem. Commun. 2018; 54: 4798
42 Hegedus LS, Sestrick MR, Michaelson ET, Harrington PJ. J. Org. Chem. 1989; 54: 4141
43 Harrington PJ, Hegedus LS. J. Org. Chem. 1984; 49: 2657
44 Larock RC, Bernhardt JC. J. Org. Chem. 1978; 43: 710

45a Beak P, Lee WK. J. Org. Chem. 1993; 58: 1109
45b Hodson FM, Madge DJ, Slawin AN. Z, Widdowson DA, Williams DJ. Tetrahedron 1994; 50: 1899

46 Labadie SS, Teng E. J. Org. Chem. 1994; 59: 4250
47 Soley R, Albericio F, Álvarez M. Synthesis 2007; 1559
48 Labadie JW, Stille JK. J. Am. Chem. Soc. 1983; 105: 6129
49 Kianmehr E, Kazemi S, Foroumadi A. Tetrahedron 2014; 70: 349
50 Yan X.-B, Shen Y.-W, Chen D.-Q, Gao P, Li Y.-X, Song X.-R, Liu X.-Y, Liang Y.-M. Tetrahedron 2014; 70: 7490
51 Li D, Wang M, Liu J, Zhao Q, Wang L. Chem. Commun. 2013; 49: 3640
52 Zhang H.-J, Wu Z, Lin W, Wen T.-B. Chin. J. Chem. 2015; 33: 517
53 Wang W, Liu J, Gui Q, Tan Z. Synlett 2015; 26: 771
54 Sharma UK, Gemoets HP, Schröder F, Noël T, Van der Eycken EV. ACS Catal. 2017; 7: 3818
55 Manna MK, Bairy G, Jana R. Org. Biomol. Chem. 2017; 15: 5899
56 Kumar G, Sekar G. RSC Adv. 2015; 5: 28292
57 Jiang H, Gao S, Xu J, Wu X, Lin A, Yao H. Adv. Synth. Catal. 2016; 358: 188
58 Hu Q, Liu X, Huang F, Wang F, Li Q, Zhang W. Catal. Commun. 2018; 113: 27
59 Luo J, Gao S, Ma Y, Ge G. Synlett 2018; 29: 969
60 Kothandapani J, Reddy SM. K, Thamotharan S, Kumar SM, Byrappa K, Ganesan SS. Eur. J. Org. Chem. 2018; 2762
61 Li C, Zhu W, Shu S, Wu X, Liu H. Eur. J. Org. Chem. 2015; 3743
62 Pd-catalyzed C3-alkylation of indoles with alcohols has been reported under non-oxidative conditions: Putra AE, Takigawa K, Tanaka H, Ito Y, Oe Y, Ohta T. Eur. J. Org. Chem. 2013; 6344
63 Park J, Kim A, Sharma S, Kim M, Park E, Jeon Y, Lee Y, Kwak JH, Jung YH, Kim IS. Org. Biomol. Chem. 2013; 11: 2766
64 Yu L, Li P, Wang L. Chem. Commun. 2013; 49: 2368
65 Pan C, Jin H, Liu X, Cheng Y, Zhu C. Chem. Commun. 2013; 49: 2933
66 The decarboxylation could be mediated by the Ag₂O/K₂S₂O₈ association: Mandal S, Bera T, Dubey G, Saha J, Laha JK. ACS Catal. 2018; 8: 5085
67 Jiang G, Wang S, Zhang J, Yu J, Zhang Z, Ji F. Adv. Synth. Catal. 2019; 361: 1798
68 Gu L.-J, Liu J.-Y, Zhang L.-Z, Xiong Y, Wang R. Chin. Chem. Lett. 2014; 25: 90
69 Ma Y, You J, Song F. Chem. Eur. J. 2013; 19: 1189
70 Jiang TS, Wang GW. Org. Lett. 2013; 15: 788
71 Das T, Chakraborty A, Sarkar A. Tetrahedron Lett. 2014; 55: 7198
72 Peng J, Liu L, Hu Z, Huang J, Zhu Q. Chem. Commun. 2012; 48: 3772
73 Peng J, Zhao J, Hu Z, Liang D, Huang J, Zhu Q. Org. Lett. 2012; 14: 4966
74 Tulichala RN. P, Shankar M, Swamy KC. K. J. Org. Chem. 2018; 83: 4375
75 Nandi D, Jhou Y.-M, Lee J.-Y, Kuo B.-C, Liu C.-Y, Huang P.-W, Lee HM. J. Org. Chem. 2012; 77: 9384
76 Tang RY, Guo XK, Xiang JN, Li JH. J. Org. Chem. 2013; 78: 11163
77 For an efficient procedure under Cu catalysis, see: Wu J.-C, Song R.-J, Wang Z.-Q, Huang X.-C, Xie Y.-X, Li J.-H. Angew. Chem. Int. Ed. 2012; 51: 3453
78 Li Y, Xue D, Lu W, Fan X, Wang C, Xiao J. RSC Adv. 2013; 3: 11463
79 For a review on dehydrogenative Heck reactions, see: Le Bras J, Muzart J. Chem. Rev. 2011; 111: 1170
80 Zhao Y, Sharma UK, Schröder F, Sharma N, Song G, Van der Eycken EV. RSC Adv. 2017; 7: 32559
81 Anhydrous t-BuOOH solution (5.5 M in decane over molecular sieves) was used: Sharma, U. K. personal communication, 2018.
82 Song H, Chen D, Pi C, Cui X, Wu Y. J. Org. Chem. 2014; 79: 2955
83 Bao Y, Wang J.-Y, Zhang Y.-X, Li Y, Wang X.-S. Tetrahedron Lett. 2018; 59: 3147

84a Baeyer A. Ann. Chem. Pharm. 1866; 140: 295
84b Baeyer A, Emmerling A. Ber. Dtsch. Chem. Ges. 1869; 2: 679