Synthesis of 1,1-Disubstituted Indenes via Palladium-Catalyzed Cross-Coupling of ortho-Alkenyl Bromobenzenes and α-Aryl-α-diazoesters

Dedication to Professor Guo-Qiang Lin on the Occasion of his 80th Birthday

Abstract

Palladium-catalyzed cross-coupling of ortho-alkenyl bromobenzenes and α-aryl-α-diazoesters was realized. The reactions proceeded in moderate to excellent yields with broad substrate scope, providing a straightforward method for the synthesis of 1,1-disubstituted indenes. The reaction is thought to undergo a tandem alkenyl C–H activation/carbene insertion sequence, in which a C,C-pallada(II)cycle is the key intermediate.

Key words

palladium catalyst - alkenyl C–H activation - carbene insertion - indene

• References

• 1a Pluskota R, Koba M. Mini-Rev. Med. Chem. 2018; 18: 1321
• 1b Prasher P, Sharma M. ChemistrySelect 2021; 6: 2658
• 2 Li Y.-F. Chem. Asian J. 2013; 8: 2316
• 3a Rogers JS, Lachicotte RJ, Bazan GC. Organometallics 1999; 18: 3976
• 3b Fischer M, Oswald T, Ebert H, Schmidtmann M, Beckhaus R. Organometallics 2018; 37: 415
• 4a Gabriele B, Mancuso R, Veltri L. Chem. Eur. J. 2016; 22: 5056
• 4b He Q, Yin Z, Chen H, Zhang Z, Wang X, Yue G. Prog. Chem. 2016; 28: 801
• 4c Rinaldi A, Scarpi D, Occhiato EG. Eur. J. Org. Chem. 2019; 7401
• 4d Shi CX, Feng C.-G, Chen Y.-L, Zhang S.-S, Lin G.-Q. Chin. J. Org. Chem. 2020; 40: 817
• 5a Hitce J, Baudoin O. Adv. Synth. Catal. 2007; 349: 2054
• 5b Mazuela J, Banerjee D, Bäckvall JE. J. Am. Chem. Soc. 2015; 137: 9559
• 5c Barroso R, Paraja M, Cabal M.-P, Valdés C. Org. Lett. 2017; 19: 4086
• 5d Liu X.-W, Li S.-S, Dai D.-T, Zhao M, Shan C.-C, Xu Y.-H, Loh T.-P. Org. Lett. 2019; 21: 3696
• 6a Sanjuán AM, Virumbrales C, García-García P, Fernández-Rodríguez MA, Sanz R. Org. Lett. 2016; 18: 1072
• 6b Nahide PD, Jiménez-Halla JO. C, Wrobel K, Solorio-Alvarado CR, Alvarado RO, Yahuaca-Juárez B. Org. Biomol. Chem. 2018; 16: 7330
• 7 Egi M, Shimizu K, Kamiya M, Ota Y, Akai S. Chem. Commun. 2015; 51: 380
• 8a Fang X, Yu P, Willems S, Morandi B. Helv. Chim. Acta 2019; 102: e1900059
• 8b Zhang T, Luan Y.-X, Zheng S.-J, Peng Q, Ye M. Angew. Chem. Int. Ed. 2020; 59: 7439
• 9 Wang M, Bai D, Kong L, Liu B, Li X. Org. Lett. 2018; 20: 7775
• 10a Zhang D, Liu Z, Yum EK, Larock RC. J. Org. Chem. 2007; 72: 251
• 10b Chidipudi SR, Khan I, Lam HW. Angew. Chem. Int. Ed. 2012; 51: 12115
• 10c Jia X, Petrone DA, Lautens M. Angew. Chem. Int. Ed. 2012; 51: 9870
• 10d Dooley JD, Chidipudi SR, Lam HW. J. Am. Chem. Soc. 2013; 135: 10829
• 10e Ramesh K, Satyanarayana G. J. Org. Chem. 2017; 82: 4254
• 11 García-López J.-A, Saura-Llamas I. Eur. J. Inorg. Chem. 2021; 3655
• 12 Rahím A, Feng J, Gu Z. Chin. J. Chem. 2019; 37: 929
• 13 Hu T.-J, Zhang G, Chen Y.-H, Feng C.-G, Lin G.-Q. J. Am. Chem. Soc. 2016; 138: 2897
• 14a Hu T.-J, Li M.-Y, Zhao Q, Feng C.-G, Lin G.-Q. Angew. Chem. Int. Ed. 2018; 57: 5871
• 14b Xue Z.-J, Li M.-Y, Zhu B.-B, He Z.-T, Feng C.-G, Lin G.-Q. Adv. Synth. Catal. 2021; 363: 2089
• 15 Wei D, Hu T.-J, Feng C.-G, Lin G.-Q. Chin. J. Chem. 2018; 36: 743
• 16 Li M.-Y, Han P, Hu T.-J, Wei D, Zhang G, Qin A, Feng C.-G, Tang BZ, Lin G.-Q. Iscience 2020; 23: 100966
• 17 Wei D, Li M.-Y, Zhu B.-B, Yang X.-D, Zhang F, Feng C.-G, Lin G.-Q. Angew. Chem. Int. Ed. 2019; 58: 16543
• 18 Zhu B.-B, Ye W.-B, He Z.-T, Zhang S.-S, Feng C.-G, Lin G.-Q. ACS Catal. 2021; 11: 12123
• 19 Zhang G, Feng X.-J, Li M.-Y, Ji X.-M, Lin G.-Q, Feng C.-G. Org. Biomol. Chem. 2022; 20: 5383
• 20 Xu S, Chen R, Fu Z, Zhou Q, Zhang Y, Wang J. ACS Catal. 2017; 7: 1993
• 21 Wakioka M, Nakamura Y, Montgomery M, Ozawa F. Organometallics 2015; 34: 198
• 22 CCDC 2226861 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures
• 23a Wang L, Carrow BP. ACS Catal. 2019; 9: 6821
• 23b Lapointe D, Fagnou K. Chem. Lett. 2010; 39: 1118
• 23c Lafrance M, Rowley CN, Woo TK, Fagnou K. J. Am. Chem. Soc. 2006; 128: 8754