Intramolecular Ynamide-Benzyne (3+2) Cycloadditions.
Benzyne
Cycloaddition
Heterocycles
Ylides
Ynamides
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
02 May 2023
02 May 2023
Historique:
received:
17
01
2023
medline:
10
3
2023
pubmed:
10
3
2023
entrez:
9
3
2023
Statut:
ppublish
Résumé
We report herein intramolecular (3+2) cycloaddition reactions between ynamides as three-atom components and benzyne. In these intramolecular reactions, the two-bond formation is realized by exploiting benzyne precursors that contain a chlorosilyl group as a linking functionality. This method thus highlights the ambivalent character of the intermediate indolium ylide, which exhibits both nucleophilic and electrophilic properties at its C2 atom.
Identifiants
pubmed: 36895082
doi: 10.1002/anie.202300907
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202300907Subventions
Organisme : Japan Society for the Promotion of Science
ID : 21H02068
Organisme : Japan Society for the Promotion of Science
ID : 21H05211
Organisme : Shionogi
Organisme : Japan Science Society
ID : Sasakawa Scientific Research Grant
Organisme : Japan Science and Technology Agency
ID : the establishment of university fellowships towards the creation of science technology innovation - JPMJFS2123
Organisme : Japan Agency for Medical Research and Development
ID : 22ama121042j0001
Organisme : Japan Agency for Medical Research and Development
ID : 22ama121034j0001
Informations de copyright
© 2023 Wiley-VCH GmbH.
Références
R. Huisgen, A. Eckell, Tetrahedron Lett. 1960, 1, 5-8;
R. Huisgen, H. Stangl, H. J. Sturm, H. Wagenhofer, Angew. Chem. Int. Ed. Engl. 1962, 1, 50;
Angew. Chem. 1962, 74, 31;
R. Huisgen, M. Seidel, G. Wallbillich, H. Knupfer, Tetrahedron 1962, 17, 3-29;
R. Huisgen, R. Grashey, E. Steingruber, Tetrahedron Lett. 1963, 4, 1441-1445; For a recent review, see:
M. Breugst, H.-U. Reissig, Angew. Chem. Int. Ed. 2020, 59, 12293-12307;
Angew. Chem. 2020, 132, 12389-12404.
A. T. Biju, Modern Aryne Chemistry, Wiley-VCH, Weinheim, 2021.
R. Huisgen, R. Knorr, Naturwissenschaften 1961, 48, 716;
G. Wittig, R. W. Hoffmann, Angew. Chem. 1961, 73, 435-436;
F. Shi, J. P. Waldo, Y. Chen, R. C. Larock, Org. Lett. 2008, 10, 2409-2412;
S. Chandrasekhar, M. Seenaiah, C. h. L. Rao, C. h. R. Reddy, Tetrahedron 2008, 64, 11325-11327;
L. Campbell-Verduyn, P. H. Elsinga, L. Mirfeizi, R. A. Dierckx, B. L. Feringa, Org. Biomol. Chem. 2008, 6, 3461-3463;
T. Ikawa, A. Takagi, M. Goto, Y. Aoyama, Y. Ishikawa, Y. Itoh, S. Fujii, H. Tokiwa, S. Akai, J. Org. Chem. 2013, 78, 2965-2983;
A. Guin, R. N. Gaykar, S. Bhattacharjee, A. T. Biju, J. Org. Chem. 2019, 84, 12692-12699.
G. Baum, R. Bernard, H. Shechter, J. Am. Chem. Soc. 1967, 89, 5307-5308;
T. Jin, Y. Yamamoto, Angew. Chem. Int. Ed. 2007, 46, 3323-3325;
Angew. Chem. 2007, 119, 3387-3389;
Z. Liu, F. Shi, P. D. G. Martinez, C. Raminelli, R. C. Larock, J. Org. Chem. 2008, 73, 219-226;
P. Li, C. Wu, J. Zhao, D. C. Rogness, F. Shi, J. Org. Chem. 2012, 77, 3149-3158;
B. Cheng, B. Zu, B. Bao, Y. Li, R. Wang, H. Zhai, J. Org. Chem. 2017, 82, 8228-8233;
B. V. Subba Reddy, R. R. Gopi Reddy, V. Reddy Thummaluru, B. Sridhar, ChemistrySelect 2017, 2, 4290-4293.
J. A. Crossley, D. L. Browne, Tetrahedron Lett. 2010, 51, 2271-2273;
C. Spiteri, C. Mason, F. Zhang, D. J. Ritson, P. Sharma, S. Keeling, J. E. Moses, Org. Biomol. Chem. 2010, 8, 2537-2542;
A. V. Dubrovskiy, P. Jain, F. Shi, G. H. Lushington, C. Santini, P. Porubsky, R. C. Larock, ACS Comb. Sci. 2013, 15, 193-201.
C. Spiteri, S. Keeling, J. E. Moses, Org. Lett. 2010, 12, 3368-3371;
A. Kowalczyk, G. Utecht-Jarzyńska, G. Mlostoń, M. Jasiński, J. Fluorine Chem. 2021, 241, 109691.
H. H. Wasserman, J. M. Fernandez, J. Am. Chem. Soc. 1968, 90, 5322-5323.
T. Matsuzawa, T. Hosoya, S. Yoshida, Chem. Sci. 2020, 11, 9691-9696.
A. Pommainville, D. Campeau, F. Gagosz, Angew. Chem. Int. Ed. 2022, 61, e202205963;
Angew. Chem. 2022, 134, e202205963.
For representative examples of aryne-based indole synthesis, see:
L. Lalloz, P. Caubère, J. Chem. Soc. Chem. Commun. 1975, 745;
V. Nair, K. H. Kim, J. Org. Chem. 1975, 40, 3784-3786;
D. Hong, Z. Chen, X. Lin, Y. Wang, Org. Lett. 2010, 12, 4608-4611;
D. McAusland, S. Seo, D. G. Pintori, J. Finlayson, M. F. Greaney, Org. Lett. 2011, 13, 3667-3669;
L. He, J.-X. Pian, J.-F. Shi, G.-F. Du, B. Dai, Tetrahedron 2014, 70, 2400-2405;
M. Thangaraj, S. S. Bhojgude, S. Jain, R. G. Gonnade, A. T. Biju, J. Org. Chem. 2016, 81, 8604-8611;
S. Yaragorla, D. Arun, J. Org. Chem. 2022, 87, 14250-14263.
R. Knorr, Chem. Rev. 2004, 104, 3795-3850.
For selected reviews, see:
C. A. Zificsak, J. A. Mulder, R. P. Hsung, C. Rameshkumar, L.-L. Wei, Tetrahedron 2001, 57, 7575-7606;
G. Evano, A. Coste, K. Jouvin, Angew. Chem. Int. Ed. 2010, 49, 2840-2859;
Angew. Chem. 2010, 122, 2902-2921;
K. A. DeKorver, H. Li, A. G. Lohse, R. Hayashi, Z. Lu, Y. Zhang, R. P. Hsung, Chem. Rev. 2010, 110, 5064-5106;
X.-N. Wang, H.-S. Yeom, L.-C. Fang, S. He, Z.-X. Ma, B. L. Kedrowski, R. P. Hsung, Acc. Chem. Res. 2014, 47, 560-578;
G. Duret, V. Le Fouler, P. Bisseret, V. Bizet, N. Blanchard, Eur. J. Org. Chem. 2017, 6816-6830;
A. Sahoo, B. Prabagar, N. Ghosh, A. K. Sahoo, Synlett 2017, 28, 2539-2555;
R. H. Dodd, K. Cariou, Chem. Eur. J. 2018, 24, 2297-2304;
C. Mahe, K. Cariou, Adv. Synth. Catal. 2020, 362, 4820-4832;
Q. Li, L. Han, L. Zhao, Y. Hou, R. Sharma, Synth. Commun. 2021, 51, 2754-2781;
T.-D. Tan, Z.-S. Wang, P.-C. Qian, L.-W. Ye, Small Methods 2021, 5, 2000673.
D. Campeau, A. Pommainville, F. Gagosz, J. Am. Chem. Soc. 2021, 143, 9601-9611.
J. Ficini, A. Krief, Tetrahedron Lett. 1968, 9, 4143-4146.
Our preliminary attempts at the intermolecular reaction between benzyne and ynamides gave the corresponding indole in only 21 % yield, even after optimization of the reaction conditions. For details, see the Supporting Information.
A. Nishii, H. Takikawa, K. Suzuki, Chem. Sci. 2019, 10, 3840-3845;
H. Takikawa, A. Nishii, H. Takiguchi, H. Yagishita, M. Tanaka, K. Hirano, M. Uchiyama, K. Ohmori, K. Suzuki, Angew. Chem. Int. Ed. 2020, 59, 12440-12444;
Angew. Chem. 2020, 132, 12540-12544;
T. Tawatari, K. Takasu, H. Takikawa, Chem. Commun. 2021, 57, 11863-11866;
T. Tawatari, R. Kato, K. Takasu, H. Takikawa, Synthesis 2022, 54, 4979-4988.
Using a combination of Cs2CO3 and 18-crown-6, rather than fluoride ions such as KF and TBAF, effectively promotes the generation of benzyne by selectively activating the trimethylsilyl group while keeping the silicon tether intact. For details, see refs. 16c and 16d.
All attempts to trap indolium-ylide intermediate H by an appropriate electrophile prior to the protonation at C2 have remained unsuccessful so far. For details, see the Supporting Information.
F. Giraud, C. Loge, F. Pagniez, D. Crepin, S. Barres, C. Picot, P. Le Pape, M. Le Borgne, J. Enzyme Inhib. Med. Chem. 2009, 24, 1067-1075.
M. Le Borgne, P. Marchand, M. Duflos, B. Delevoye-Seiller, S. Piessard-Robert, G. Le Baut, R. W. Hartmann, M. Palzer, Arch. Pharm. Pharm. Med. Chem. 1997, 330, 141-145;
T. Sumiya, M. Ishigaki, K. Oh, Int. J. Chem. Eng. Appl. 2017, 8, 233-236.
Z. Li, J. Hong, X. Zhou, Tetrahedron 2011, 67, 3690-3697.
S. Tang, J.-H. Li, Y.-X. Xie, N.-X. Wang, Synthesis 2007, 10, 1535-1541.
J. Xu, L. Liang, H. Zheng, Y. R. Chi, R. Tong, Nat. Commun. 2019, 10, 4754.
No other isolable products were detected. Although the (2+2) cycloaddition might compete, the corresponding cycloadduct that contains an anti-aromatic benzocyclobutadiene structure would be prone to decomposition.
T. Ikawa, S. Masuda, T. Nishiyama, A. Takagi, S. Akai, Aust. J. Chem. 2014, 67, 475-480.
Substrate S58 with a C−O instead of the Si−O tether also smoothly underwent the cycloaddition to furnish the corresponding indole S59, albeit in moderate yield. For details, see the Supporting Information.
For recent experimental examples, see:
S. Zhou, G. M. Anderson, B. Mondal, E. Doni, V. Ironmonger, M. Kranz, T. Tuttle, J. A. Murphy, Chem. Sci. 2014, 5, 476-482;
Y. Hu, J. Ma, L. Li, Q. Hu, S. Lv, B. Liu, S. Wang, Chem. Commun. 2017, 53, 1542-1545;
X. Yang, G. C. Tsui, Chem. Sci. 2018, 9, 8871-8875;
M. Scherübl, C. G. Daniliuc, A. Studer, Angew. Chem. Int. Ed. 2021, 60, 711-715;
Angew. Chem. 2021, 133, 721-725. For recent theoretical examples, see:
S. Yamabe, T. Minato, T. Watanabe, T. Machiguchi, Theor. Chem. Acc. 2011, 130, 981-990;
P. Pérez, L. R. Domingo, Eur. J. Org. Chem. 2015, 2826-2834;
T. Yang, S. Nagase, T. Akasaka, J. M. Poblet, K. N. Houk, M. Ehara, X. Zhao, J. Am. Chem. Soc. 2015, 137, 6820-6828;
J. P. Martínez, F. Langa, F. M. Bickelhaupt, S. Osuna, M. Solà, J. Phys. Chem. C 2016, 120, 1716-1726;
A. Comandini, S. Abid, N. Chaumeix, J. Phys. Chem. A 2017, 121, 5921-5931;
T. Ikawa, Y. Yamamoto, A. Heguri, Y. Fukumoto, T. Murakami, A. Takagi, Y. Masuda, K. Yahata, H. Aoyama, Y. Shigeta, H. Tokiwa, S. Akai, J. Am. Chem. Soc. 2021, 143, 10853-10859;
Y. Hashimoto, D. J. Tantillo, J. Org. Chem. 2022, 87, 12954-12962;
L. Monluc, A. A. Nikolayev, I. A. Medvedkov, V. N. Azyazov, A. N. Morozov, A. M. Mebel, ChemPhysChem 2022, 23, e202100758.
Indole 4 was obtained in 58 % yield, without any isolable by-product(s). Even if formed, the short-lived diradical IM2 would be less sensitive to external molecules in the reaction medium.
The corresponding phenyl adduct S38 (11 %) and 2-tosylindole S37 (7 %) resulting from 1,2-migration of the N-tosyl group were identified as other by-products. For details including other substrates in this context, see the Supporting Information.
The N-tosyl leaving group is crucial, as the reaction of the corresponding N-Boc derivative resulted in the formation of a complex mixture, since the Boc group is an unsuitable leaving group. For selected examples of SN2 reactions on a nitrogen atom, see:
T. Hatakeyama, Y. Yoshimoto, S. K. Ghorai, M. Nakamura, Org. Lett. 2010, 12, 1516-1519;
S. Yoshida, K. Igawa, K. Tomooka, J. Am. Chem. Soc. 2012, 134, 19358-19361;
J. J. Sirois, B. DeBoef, Tetrahedron Lett. 2015, 56, 5610-5612.
The reaction was attempted with an excess of alkene to capture the intermediary vinylidene, albeit that any corresponding “interrupted” product was not observed. For details, see the Supporting Information.
R. R. Tykwinski, J. A. Whiteford, P. J. Stang, J. Chem. Soc. Chem. Commun. 1993, 1800-1801;
T. Shu, D.-W. Chen, M. Ochiai, Tetrahedron Lett. 1996, 37, 5539-5542;
K. S. Feldman, M. M. Bruendl, K. Schildknegt, A. C. Bohnstedt, J. Org. Chem. 1996, 61, 5440-5452;
S. Nikas, N. Rodios, A. Varvoglis, Molecules 2000, 5, 1182-1186;
A. R. Petrov, C. G. Daniliuc, P. G. Jones, M. Tamm, Chem. Eur. J. 2010, 16, 11804-11808.