Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2021; 32(12): 1169-1178
DOI: 10.1055/a-1471-7307
DOI: 10.1055/a-1471-7307
synpacts
Allenes: Versatile Building Blocks in Cobalt-Catalyzed C–H Activation
We would like to thank the Science and Engineering Research Board (SERB), India, for their generous financial support (CRG/2019/005059).
Abstract
The unique reactivity of allenes has led to their emergence as valuable coupling partners in transition-metal-mediated C–H activation reactions. On the other hand, due to its high abundance and high Lewis acidity, cobalt is garnering widespread interest as a useful catalyst for C–H activation. Here, we summarize cobalt-catalyzed C–H activations involving allenes as coupling partners and then describe our studies on Co(III)-catalyzed C-8 dienylation of quinoline N-oxides with allenes bearing a leaving group at the α-position for realizing a dienylation protocol.
Publication History
Received: 03 March 2021
Accepted after revision: 31 March 2021
Accepted Manuscript online:
31 March 2021
Article published online:
28 April 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Zimmer R, Dinesh CU, Nandanan E, Khan FA. Chem. Rev. 2000; 100: 3067
- 1b Blieck R, Taillefer M, Monnier F. Chem. Rev. 2020; 120: 13545
- 1c Ma S. Acc. Chem. Res. 2003; 36: 701
- 1d Hoffmann-Röder A, Krause N. Angew. Chem. Int. Ed. 2004; 43: 1196
- 1e Cowen BJ, Miller SJ. Chem. Soc. Rev. 2009; 38: 3102
- 1f Yu S, Ma S. Angew. Chem. Int. Ed. 2012; 51: 3074
- 1g Lu T, Lu Z, Ma Z.-X, Zhang Y, Hsung RP. Chem. Rev. 2013; 113: 4862
- 2a Yang B, Qiu Y, Bäckvall J.-E. Acc. Chem. Res. 2018; 51: 1520
- 2b Ye J, Ma S. Acc. Chem. Res. 2014; 47: 989
- 2c Aubert C, Fensterbank L, Garcia P, Malacria M, Simonneau A. Chem. Rev. 2011; 111: 1954
- 2d Ma S. Chem. Rev. 2005; 105: 2829
- 3 Hashmi AS. K. Angew. Chem. Int. Ed. 2000; 39: 3590
- 4 Santhoshkumar R, Cheng C.-H. Asian J. Org. Chem. 2018; 7: 1151
- 5 Zhang YJ, Skucas E, Krische MJ. Org. Lett. 2009; 11: 4248
- 6 Tran DN, Cramer N. Angew. Chem. Int. Ed. 2010; 49: 8181
- 7a Kong D.-S, Wang Y.-F, Zhao Y.-S, Li Q.-H, Chen Y.-X, Tian P, Lin G.-Q. Org. Lett. 2018; 20: 1154
- 7b Jia Z.-J, Merten C, Gontla R, Danilicu CG, Antonchick AP, Waldmann H. Angew. Chem. Int. Ed. 2017; 56: 2429
- 7c Zhou Z, Liu G, Lu X. Org. Lett. 2016; 18: 5668
- 7d Ye B, Cramer N. J. Am. Chem. Soc. 2013; 135: 636
- 7e Wang H, Beiring B, Yu D.-G, Collins KD, Glorius F. Angew. Chem. Int. Ed. 2013; 52: 12430
- 7f Gong T.-J, Su W, Liu Z.-J, Cheng W.-M, Xiao B, Fu Y. Org. Lett. 2014; 16: 330
- 7g Ghosh C, Nagtilak PJ, Kapur M. Org. Lett. 2019; 21: 3237
- 7h Zeng R, Ye J, Fu C, Ma S. Adv. Synth. Catal. 2013; 355: 1963
- 7i Zeng R, Fu C, Ma S. J. Am. Chem. Soc. 2012; 134: 9597
- 7j Wang H, Glorius F. Angew. Chem. Int. Ed. 2012; 51: 7318
- 8 Nakanowatari S, Ackermann L. Chem. Eur. J. 2015; 21: 16246
- 9 Nakanowatari S, Müller T, Oliveira JC. A, Ackermann L. Angew. Chem. Int. Ed. 2017; 56: 15891
- 10a Chen S.-Y, Han X.-L, Wu J.-Q, Li Q, Chen Y, Wang H. Angew. Chem. Int. Ed. 2017; 56: 9939
- 10b Chen S.-Y, Li Q, Liu X.-G, Wu J.-Q, Zhang S.-S, Wang H. ChemSusChem 2017; 10: 2360
- 10c Chen S.-Y, Li Q, Wang H. J. Org. Chem. 2017; 82: 11173
- 11 Mo J, Müller T, Oliveira JC. A, Ackermann L. Angew. Chem. Int. Ed. 2018; 57: 7719
- 12 Kuppusamy R, Muralirajan K, Cheng C.-H. ACS Catal. 2016; 6: 3909
- 13 Kuppusamy R, Santhoshkumar R, Boobalan R, Wu H.-R, Cheng C.-H. ACS Catal. 2018; 8: 1880
- 14 Boobalan R, Santhoshkumar R, Cheng C.-H. Adv. Synth. Catal. 2019; 361: 1140
- 15 Boerth JA, Ellman JA. Angew. Chem. Int. Ed. 2017; 56: 9976
- 16 Nakanowatari S, Mei R, Feldt M, Ackermann L. ACS Catal. 2017; 7: 2511
- 17 Thrimurtulu N, Dey A, Maiti D, Volla CM. R. Angew. Chem. Int. Ed. 2016; 55: 12361
- 18a Li T, Zhang C, Tan Y, Pan W, Rao Y. Org. Chem. Front. 2017; 4: 204
- 18b Boobalan R, Kuppusamy R, Santhoshkumar R, Gandeepan P, Cheng C.-H. ChemCatChem 2017; 9: 273
- 18c Lan T, Wang L, Rao Y. Org. Lett. 2017; 19: 972
- 19 Zhai S, Qiu S, Chen X, Tao C, Li Y, Cheng B, Wang H, Zhai H. ACS Catal. 2018; 8: 6645
- 20 Meyer TH, Oliveira JC. A, Sau SC. S, Ang NW. J, Ackermann L. ACS Catal. 2018; 8: 9140. 25
- 21 Mei R, Fang X, He L, Sun J, Zou L, Ma W, Ackermann L. Chem. Commun. 2020; 56: 1393
- 22a Yoshino T, Ikemoto H, Matsunaga S, Kanai M. Angew. Chem. Int. Ed. 2013; 52: 2207
- 22b Moselage M, Li J, Ackermann L. ACS Catal. 2016; 6: 498
- 22c Yoshino T, Matsunaga S. Adv. Synth. Catal. 2017; 359: 1245
- 23 Zaitsev VG, Shabashov D, Daugulis O. J. Am. Chem. Soc. 2005; 127: 13154
- 24 Grigorjeva L, Daugulis O. Angew. Chem. Int. Ed. 2014; 53: 10209
- 25a Thrimurtulu N, Nallagonda R, Volla CM. R. Chem. Commun. 2017; 53: 1872
- 25b Dey A, Thrimurtulu N, Volla CM. R. Org. Lett. 2019; 21: 3871
- 25c Dey A, Volla CM. R. Org. Lett. 2020; 22: 7480
- 26a Li Q, Fu C, Ma S. Angew. Chem. Int. Ed. 2012; 51: 11783
- 26b Fu C, Ma S. Angew. Chem. Int. Ed. 2014; 53: 6511
- 26c Petrone DA, Isomura M, Franzoni I, Rössler SL, Carreira EM. J. Am. Chem. Soc. 2018; 140: 4697
- 27a Lippincott DJ, Linstadt RT. H, Maser MR, Gallou F, Lipshutz BH. Org. Lett. 2018; 20: 4719
- 27b Semba K, Fujihara T, Terao J, Tsuji Y. Angew. Chem. Int. Ed. 2013; 52: 12400
- 27c Mao M, Zhang L, Chen Y.-Z, Zhu J, Wu L. ACS Catal. 2017; 7: 181
- 27d Zhu J, Mao M, Ji H.-J, Xu J.-Y, Wu L. Org. Lett. 2017; 19: 1946
- 28 Shukla RS, Nair AM, Khan S, Volla CM. R. Angew. Chem. Int. Ed. 2020; 59: 17042
- 29 Sontakke GS, Shukla RS, Volla CM. R. Beilstein J. Org. Chem. 2021; 17: 485
For Rh-catalyzed C–H activation reactions using allenes, see: