Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions

Pascal Matton; Steve Huvelle; Mansour Haddad; Phannarath Phansavath; Virginie Ratovelomanana-Vidal

doi:10.1055/s-0040-1719831

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(01): 4-32
DOI: 10.1055/s-0040-1719831

review

Recent Progress in Metal-Catalyzed [2+2+2] Cycloaddition Reactions

Pascal Matton

,

Steve Huvelle

,

Mansour Haddad

,

Phannarath Phansavath

,

Virginie Ratovelomanana-Vidal ∗

Abstract

Alle Artikel dieser Rubrik

Abstract

Metal-catalyzed [2+2+2] cycloaddition is a powerful tool that allows rapid construction of functionalized 6-membered carbo- and heterocycles in a single step through an atom-economical process with high functional group tolerance. The reaction is usually regio- and chemoselective although selectivity issues can still be challenging for intermolecular reactions involving the cross-[2+2+2] cycloaddition of two or three different alkynes and various strategies have been developed to attain high selectivities. Furthermore, enantioselective [2+2+2] cycloaddition is an efficient means to create central, axial, and planar chirality and a variety of chiral organometallic complexes can be used for asymmetric transition-metal-catalyzed inter- and intramolecular reactions. This review summarizes the recent advances in the field of [2+2+2] cycloaddition.

1 Introduction

2 Formation of Carbocycles

2.1 Intermolecular Reactions

2.1.1 Cyclotrimerization of Alkynes

2.1.2 [2+2+2] Cycloaddition of Two Different Alkynes

2.1.3 [2+2+2] Cycloaddition of Alkynes/Alkenes with Alkenes/Enamides

2.2 Partially Intramolecular [2+2+2] Cycloaddition Reactions

2.2.1 Rhodium-Catalyzed [2+2+2] Cycloaddition

2.2.2 Molybdenum-Catalyzed [2+2+2] Cycloaddition

2.2.3 Cobalt-Catalyzed [2+2+2] Cycloaddition

2.2.4 Ruthenium-Catalyzed [2+2+2] Cycloaddition

2.2.5 Other Metal-Catalyzed [2+2+2] Cycloaddition

2.3 Totally Intramolecular [2+2+2] Cycloaddition Reactions

3 Formation of Heterocycles

3.1 Cycloaddition of Alkynes with Nitriles

3.2 Cycloaddition of 1,6-Diynes with Cyanamides

3.3 Cycloaddition of 1,6-Diynes with Selenocyanates

3.4 Cycloaddition of Imines with Allenes or Alkenes

3.5 Cycloaddition of (Thio)Cyanates and Isocyanates

3.6 Cycloaddition of 1,3,5-Triazines with Allenes

3.7 Cycloaddition of Aldehydes with Enynes or Allenes/Alkenes

3.8 Totally Intramolecular [2+2+2] Cycloaddition Reactions

4 Conclusion

Key words

cycloaddition - cyclotrimerization - transition metal - arenes - heterocycles - asymmetric catalysis - alkynes - homogeneous catalysis

Volltext

Referenzen

References

1a Berthelot M. Justus Liebigs Ann. Chem. 1866; 139: 272
1b Berthelot M. C R. Hebd. Seances Acad. Sci. 1866; 63: 905

2 Reppe W, Schweckendiek WJ. Justus Liebigs Ann. Chem. 1948; 560: 104
3 Hill JE, Balaich G, Fanwick PE, Rothwell IP. Organometallics 1993; 12: 2911
4 Vollhardt KP. C. Angew. Chem. Int. Ed. Engl. 1984; 23: 539
5 Ojima I, Tzamarioudaki M, Li Z, Donovan RJ. Chem. Rev. 1996; 96: 635
6 Lautens M, Klute W, Tam W. Chem. Rev. 1996; 96: 49
7 Saito S, Yamamoto Y. Chem. Rev. 2000; 100: 2901
8 Kirchner K, Calhorda MJ, Schmid R, Veiros LF. J. Am. Chem. Soc. 2003; 125: 11721
9 Rubin M, Sromek AW, Gevorgyan V. Synlett 2003; 2265
10 Kotha S, Brahmachary E, Lahiri K. Eur. J. Org. Chem. 2005; 2005: 4741
11 Yamamoto Y. Curr. Org. Chem. 2005; 9: 503
12 Gandon V, Aubert C, Malacria M. Chem. Commun. 2006; 2209
13 Tanaka K. Synlett 2007; 1977
14 Agenet N, Buisine O, Slowinski F, Gandon V, Aubert C, Malacria M. In Organic Reactions, Vol. 68. Overman LE. John Wiley & Sons; Hoboken: 2007: 1
15 Hess W, Treutwein J, Hilt G. Synthesis 2008; 3537

16a Varela J, Saá C. Synlett 2008; 2571
16b Varela JA, Saá C. J. Organomet. Chem. 2009; 694: 143

17 Galan BR, Rovis T. Angew. Chem. Int. Ed. 2009; 48: 2830
18 Pla-Quintana A, Roglans A. Molecules 2010; 15: 9230
19 Handbook of Cyclization Reactions . Ma S. Wiley-VCH; Weinheim: 2010
20 Hua R, Abrenica MV. A, Wang P. Curr. Org. Chem. 2011; 15: 712
21 Weding N, Hapke M. Chem. Soc. Rev. 2011; 40: 4525
22 Wang C, Wan B. Chin. Sci. Bull. 2012; 57: 2338
23 Yamamoto Y. In Transition-Metal-Mediated Aromatic Ring Construction . Tanaka K. John Wiley & Sons; Hoboken: 2013: 71
24 Transition-Metal-Mediated Aromatic Ring Construction. Tanaka K. John Wiley & Sons; Hoboken: 2013
25 Kumar P, Louie J. In Transition-Metal-Mediated Aromatic Ring Construction . Tanaka K. John Wiley & Sons; Hoboken: 2013: 37
26 Okamoto S, Sugiyama Y. Synlett 2013; 24: 1044
27 Thakur A, Louie J. Acc. Chem. Res. 2015; 48: 2354
28 Jungk P, Täufer T, Thiel I, Hapke M. Synthesis 2016; 48: 2026
29 Sato Y, Nishimata T, Mori M. J. Org. Chem. 1994; 59: 6133
30 Stará IG, Starý I, Kollárovič A, Teplý F, Vyskočil S, Saman D. Tetrahedron Lett. 1999; 40: 1993
31 Shibata T, Tsuchikama K. Org. Biomol. Chem. 2008; 6: 1317
32 Tanaka K. Chem. Asian J. 2009; 4: 508
33 Inglesby P, Evans PA. Chem. Soc. Rev. 2010; 39: 2791
34 Shibata T, Uchiyama T, Hirashima H, Endo K. Pure Appl. Chem. 2011; 83: 597
35 Domínguez G, Pérez-Castells J. Chem. Soc. Rev. 2011; 40: 3430
36 Marinetti A, Jullien H, Voituriez A. Chem. Soc. Rev. 2012; 41: 4884
37 Shibata Y, Tanaka K. Synthesis 2012; 44: 323
38 Broere DL. J, Ruijter E. Synthesis 2012; 44: 2639
39 Varela JA, Saá C. Chem. Rev. 2003; 103: 3787
40 Chopade PR, Louie J. Adv. Synth. Catal. 2006; 348: 2307
41 D’Souza DM, Müller TJ. Chem. Soc. Rev. 2007; 36: 1095
42 Heller B, Hapke M. Chem. Soc. Rev. 2007; 36: 1085
43 Perreault S, Rovis T. Chem. Soc. Rev. 2009; 38: 3149
44 Shaaban MR, El-Sayed R, Elwahy AH. M. Tetrahedron 2011; 67: 6095
45 Tanaka K. Heterocycles 2012; 85: 1017
46 Yamamoto Y. Heterocycles 2013; 87: 2459
47 Allais C, Grassot J.-M, Rodriguez J, Constantieux T. Chem. Rev. 2014; 114: 10829
48 Satoh Y, Obora Y. Eur. J. Org. Chem. 2015; 2015: 5041
49 Amatore M, Aubert C. Eur. J. Org. Chem. 2015; 2015: 265
50 Tanaka K, Kimura Y, Murayama K. Bull. Chem. Soc. Jpn. 2015; 88: 375
51 Lledó A, Pla-Quintana A, Roglans A. Chem. Soc. Rev. 2016; 45: 2010
52 Liu Y, Song R, Li J. Sci. China Chem. 2016; 59: 161
53 Domínguez G, Pérez-Castells J. Chem. Eur. J. 2016; 22: 6720
54 Hapke M. Tetrahedron Lett. 2016; 57: 5719
55 Yamamoto Y. Tetrahedron Lett. 2017; 58: 3787
56 Starosotnikov AM, Bastrakov MA. Chem. Heterocycl. Compd. 2017; 53: 1181
57 Babazadeh M, Soleimani-Amiri S, Vessally E, Hosseinian A, Edjlali L. RSC Adv. 2017; 7: 43716
58 Kotha S, Lahiri K, Sreevani G. Synlett 2018; 29: 2342
59 Pla-Quintana A, Roglans A. Asian J. Org. Chem. 2018; 7: 1706
60 Roglans A, Pla-Quintana A, Solà M. Chem. Rev. 2020; 121: 1894
61 Nagata T, Obora Y. Asian J. Org. Chem. 2020; 9: 1532
62 Okamoto S, Yamada T, Tanabe Y, Sakai M. Organometallics 2018; 37: 4431
63 Siemiaszko G, Six Y. New J. Chem. 2018; 42: 20219
64 Brenna D, Villa M, Gieshoff TN, Fischer F, Hapke M, Jacobi von Wangelin A. Angew. Chem. Int. Ed. 2017; 56: 8451
65 Neumeier M, Chakraborty U, Schaarschmidt D, de la Peña O’Shea V, Perez-Ruiz R, Jacobi von Wangelin A. Angew. Chem. Int. Ed. 2020; 59: 13473
66 Gawali SS, Gunanathan C. J. Organomet. Chem. 2019; 881: 139
67 Sugahara T, Guo J.-D, Sasamori T, Nagase S, Tokitoh N. Angew. Chem. Int. Ed. 2018; 57: 3499
68 Xue F, Loh YK, Song X, Teo WJ, Chua JY. D, Zhao J, Hor TS. A. Chem. Asian J. 2017; 12: 168
69 Kumon T, Yamada S, Agou T, Kubota T, Konno T. J. Fluorine Chem. 2018; 213: 11
70 García-Lacuna J, Domínguez G, Blanco-Urgoiti J, Pérez-Castells J. Org. Lett. 2018; 20: 5219
71 Ma P, Spencer JT. Inorg. Chim. Acta. 2018; 482: 67
72 Jónsson HF, Evjen S, Fiksdahl A. Org. Lett. 2017; 19: 2202
73 Tamizmani M, Sivasankar C. J. Organomet. Chem. 2017; 845: 82
74 Wang Y.-I, Hsu W.-L, Ho F.-C, Li C.-P, Wang C.-F, Chen H.-H. Tetrahedron 2017; 73: 7210
75 Weber SM, Hilt G. Org. Lett. 2019; 21: 4106
76 Doll JS, Eichelmann R, Hertwig LE, Bender T, Kohler VJ, Bill E, Wadepohl H, Roşca D.-A. ACS Catal. 2021; 11: 5593
77 Zhou F, Huang Z, Huang Z, Cheng R, Yang Y, You J. Org. Lett. 2021; 23: 4559
78 Nishigaki S, Shibata Y, Tanaka K. J. Org. Chem. 2017; 82: 11117
79 Reiner BR, Tonks IA. Inorg. Chem. 2019; 58: 10508
80 Silvestri AP, Oakdale JS. Chem. Commun. 2020; 56: 13417
81 Yang K, Wang P, Sun Z.-Y, Guo M, Zhao W, Tang X, Wang G. Org. Lett. 2021; 23: 3933
82 Hayase N, Miyauchi Y, Aida Y, Sugiyama H, Uekusa H, Shibata Y, Tanaka K. Org. Lett. 2017; 19: 2993
83 Alonso JM, Quiroga S, Codony S, Turcu AL, Barniol-Xicota M, Pérez D, Guitián E, Vázquez S, Peña D. Chem. Commun. 2018; 54: 5996
84 Wei S, Yin L, Wang SR, Tang Y. Org. Lett. 2019; 21: 1458
85 Thorve PR, Guru MM, Maji B. J. Org. Chem. 2019; 84: 8185
86 Ye F, Haddad M, Ratovelomanana-Vidal V, Michelet V. Catal. Commun. 2018; 107: 78
87 Aida Y, Shibata Y, Tanaka K. J. Org. Chem. 2018; 83: 2617
88 Jeulin S, Duprat de Paule S, Ratovelomanana-Vidal V, Genêt J.-P, Champion N, Dellis P. Angew. Chem. Int. Ed. 2004; 43: 320
89 Genêt J.-P, Ayad T, Ratovelomanana-Vidal V. Chem. Rev. 2014; 114: 2824
90 Wood JM, da Silva Júnior EN, Bower JF. Org. Lett. 2020; 22: 265
91 Manick A.-D, Salgues B, Parrain J.-L, Zaborova E, Fages F, Amatore M, Commeiras L. Org. Lett. 2020; 22: 1894
92 Artigas A, Pla-Quintana A, Lledó A, Roglans A, Solà M. Chem. Eur. J. 2018; 24: 10653
93 Aida Y, Shibata Y, Tanaka K. Chem. Asian J. 2019; 14: 1823
94 Maesato T, Shintani R. Chem. Lett. 2020; 49: 344
95 Aida Y, Shibata Y, Tanaka K. Chem. Eur. J. 2020; 26: 3004
96 Riveira MJ, Diez CM, Mischne MP, Mata EG. J. Org. Chem. 2018; 83: 10001
97 Ni J, Chen J, Zhou Y, Wang G, Li S, He Z, Sun W, Fan B. Adv. Synth. Catal. 2019; 361: 3543
98 Teng Q, Mao W, Chen D, Wang Z, Tung C.-H, Xu Z. Angew. Chem. Int. Ed. 2020; 59: 2220
99 Suzuki S, Shibata Y, Tanaka K. Chem. Eur. J. 2020; 26: 3698
100 Agou T, Saruwatari S, Shirai T, Kumon T, Yamada S, Konno T, Mizuhata Y, Tokitoh N, Sei Y, Fukumoto H, Kubota T. J. Fluorine Chem. 2020; 234: 109512
101 Rycek L, Mateus M, Beytlerová N, Kotora M. Org. Lett. 2021; 23: 4511
102 Kotha S, Sreevani G. Synthesis 2018; 50: 4883
103 Kotha S, Sreevani G. Eur. J. Org. Chem. 2018; 2018: 5935
104 Xu F, Si X.-J, Wang X.-N, Kou H.-D, Chen D.-M, Liu C.-S, Du M. RSC Adv. 2018; 8: 4895
105 Méndez-Gálvez C, Böhme M, Leino R, Savela R. Eur. J. Org. Chem. 2020; 2020: 1708
106 Amakasu T, Sato K, Ohta Y, Kitazawa G, Sato H, Oumiya K, Kawakami Y, Takeuchi T, Kabe Y. J. Organomet. Chem. 2020; 905: 121006
107 Aechtner T, Barry DA, David E, Ghellamallah C, Harvey DF, de la Houpliere A, Knopp M, Malaska MJ, Pérez D, Schärer KA, Siesel BA, Vollhardt KP. C, Zitterbart R. Synthesis 2018; 50: 1053
108 Caivano I, Kaiser RP, Schnurrer F, Mosinger J, Císařová I, Nečas D, Kotora M. Catalysts 2019; 9: 942
109 Tan J.-F, Bormann CT, Perrin FG, Chadwick FM, Severin K, Cramer N. J. Am. Chem. Soc. 2019; 141: 10372
110 Liu R, Giordano L, Tenaglia A. Chem. Asian J. 2017; 12: 2245
111 Petko D, Pounder A, Tam W. Synthesis 2019; 51: 4271
112 Miguel-Ávila J, Tomás-Gamasa M, Mascareñas JL. Angew. Chem. Int. Ed. 2020; 59: 17628
113 Miura H, Tanaka Y, Nakahara K, Hachiya Y, Endo K, Shishido T. Angew. Chem. Int. Ed. 2018; 57: 6136
114 Watanabe K, Satoh Y, Kamei M, Furukawa H, Fuji M, Obora Y. Org. Lett. 2017; 19: 5398
115 Sawano T, Toyoshima Y, Takeuchi R. Inorganics 2019; 7: 138
116 Arai S, Izaki A, Amako Y, Nakajima M, Uchiyama M, Nishida A. Adv. Synth. Catal. 2019; 361: 4882
117 Zhao W.-C, Wang X, Feng J, Tian P, He Z.-T. Tetrahedron 2021; 79: 131862
118 Mitake A, Fusamae T, Kanyiva KS, Shibata T. Eur. J. Org. Chem. 2017; 2017: 7266
119 Shibata T, Fusamae T, Takano H, Sugimura N, Kanyiva KS. Asian J. Org. Chem. 2019; 8: 970
120 Kimura Y, Shibata Y, Tanaka K. Chem. Lett. 2018; 47: 806
121 Nishigaki S, Shibata Y, Nakajima A, Okajima H, Masumoto Y, Osawa T, Muranaka A, Sugiyama H, Horikawa A, Uekusa H, Koshino H, Uchiyama M, Sakamoto A, Tanaka K. J. Am. Chem. Soc. 2019; 141: 14955
122 Aida Y, Nogami J, Sugiyama H, Uekusa H, Tanaka K. Chem. Eur. J. 2020; 26: 12579
123 Yasui T, Nakazato Y, Kurisaki K, Yamamoto Y. Adv. Synth. Catal. 2021; in press,
124 Cadart T, Nečas D, Kaiser RP, Favereau L, Cisařova I, Gyepes R, Hodačova J, Kalikova K, Bednarova L, Crassous J, Kotora M. Chem. Eur. J. 2021; 27: 11279
125 Trommer V, Fischer F, Hapke M. Monatsh. Chem. 2018; 149: 755
126 Bhatt D, Patel N, Chowdhury H, Bharatam PV, Goswami A. Adv. Synth. Catal. 2018; 360: 1876
127 Murayama K, Shibata Y, Sugiyama H, Uekusa H, Tanaka K. J. Org. Chem. 2017; 82: 1136
128 Xie Y, Wu C, Jia C, Tung C.-H, Wang W. Org. Chem. Front. 2020; 7: 2196
129 Li K, Wei L, Sun M, Li B, Liu M, Li C. Angew. Chem. Int. Ed. 2021; 60: 20204
130 Kumon T, Yamada S, Agou T, Fukumoto H, Kubota T, Hammond GB, Konno T. Adv. Synth. Catal. 2021; 363: 1912
131 Cho IY, Kim WK, Ji JH, Lee JW, Seo JK, Seo J, Hong SY. J. Org. Chem. 2021; 86: 9328
132 Wang C.-S, Sun Q, García F, Wang C, Yoshikai N. Angew. Chem. Int. Ed. 2021; 60: 9627
133 Ye F, Haddad M, Michelet V, Ratovelomanana-Vidal V. Org. Chem. Front. 2017; 4: 1063
134 Ye F, Haddad M, Ratovelomanana-Vidal V, Michelet V. Org. Lett. 2017; 19: 1104
135 Ye F, Boukattaya F, Haddad M, Ratovelomanana-Vidal V, Michelet V. New J. Chem. 2018; 42: 3222
136 Ye F, Tran C, Jullien L, Le Saux T, Haddad M, Michelet V, Ratovelomanana-Vidal V. Org. Lett. 2018; 20: 4950
137 Tran C, Haddad M, Ratovelomanana-Vidal V. Synlett 2019; 30: 1891
138 Medas KM, Lesch RW, Edioma FB, Wrenn SP, Ndahayo V, Mulcahy SP. Org. Lett. 2020; 22: 3135
139 Dubovtsev AY, Shcherbakov NV, Dar’in DV, Kukushkin VY. Adv. Synth. Catal. 2020; 362: 2672
140 Tran C, Haddad M, Ratovelomanana-Vidal V. Synthesis 2019; 51: 2532
141 Kalaramna P, Bhatt D, Sharma H, Goswami A. Eur. J. Org. Chem. 2019; 2019: 4694
142 Zhou H, Chaminda Lakmal HH, Baine JM, Valle HU, Xu X, Cui X. Chem. Sci. 2017; 8: 6520
143 Kalaramna P, Bhatt D, Sharma H, Goswami A. Adv. Synth. Catal. 2019; 361: 4379
144 Liu D, Zhou D, Yang H, Li J, Cui C. Chem. Commun. 2019; 55: 12324
145 Bhatt D, Kalaramna P, Kumar K, Goswami A. Eur. J. Org. Chem. 2020; 2020: 4606
146 Peng S, Cao S, Sun J. Org. Lett. 2017; 19: 524
147 Varela I, Faustino H, Díez E, Iglesias-Sigüenza J, Grande-Carmona F, Fernández R, Lassaletta JM, Mascareñas JL, López F. ACS Catal. 2017; 7: 2397
148 Tian T, Wang X, Lv L, Li Z. Eur. J. Org. Chem. 2020; 2020: 4425
149 Hanada K, Nogami J, Miyamoto K, Hayase N, Nagashima Y, Tanaka Y, Muranaka A, Uchiyama M, Tanaka K. Chem. Eur. J. 2021; 27: 9313