Synthesis of Phenanthrenes via Palladium-Catalyzed Three-Component Domino Reaction of Aryl Iodides, Internal Alkynes, and o-Bromobenzoic Acids

Published as part of the Special Topic Domino C–H Functionalization Reaction/Cascade Catalysis

Abstract

A new palladium-catalyzed domino alkyne insertion/C–H activation/decarboxylation sequence has been developed, which provides an efficient approach for synthesizing a variety of functionalized phenanthrenes in moderate to good yields. The method shows broad substrate scope and good functional group tolerance by employing readily available materials, including aryl iodides, internal alkynes, and o-bromobenzoic acids, as three-component coupling partners.

Key words

phenanthrenes - domino reaction - C–H activation - decarboxylation - palladium-catalyzed

• References

• 1a Li M, An C, Marszalek T, Guo X, Long Y.-Z, Yin H, Gu C, Baumgarten M, Pisula W, Mullen K. Chem. Mater. 2015; 27: 2218
• 1b Wang S, Yan X, Cheng Z, Zhang H, Liu Y, Wang Y. Angew. Chem. Int. Ed. 2015; 54: 13068
• 1c Machado AM, Munaro M, Martins TD, Davila LY. A, Giro R, Caldas MJ, Atvars TD. Z, Akcelrud LC. Macromolecules 2006; 39: 3398
• 2a Lin J.-C, Yang S.-C, Hong T.-M, Yu S.-L, Shi Q, Wei L, Chen H.-Y, Yang P.-C, Lee K.-H. J. Med. Chem. 2009; 52: 1903
• 2b Wei L, Shi Q, Bastow KF, Brossi A, Morris-Natschke SL, Nakagawa-Goto K, Wu T.-S, Pan S.-L, Teng C.-M, Lee K.-H. J. Med. Chem. 2007; 50: 3674
• 2c Banwell MG, Bezos A, Burns C, Kruszelnicki I, Parish CR, Su S, Sydnes MO. Bioorg. Med. Chem. Lett. 2006; 16: 181

Selected examples, see:
• 3a Jin R, Chen Y, Liu W, Xu D, Li Y, Ding A, Guo H. Chem. Commun. 2016; 52: 9909
• 3b Matsuda T, Kato K, Goya T, Shimada S, Murakami M. Chem. Eur. J. 2016; 22: 1941
• 3c Yamamoto Y, Matsui K, Shibuya M. Chem. Eur. J. 2015; 21: 7245
• 3d Kwon Y, Cho H, Kim S. Org. Lett. 2013; 15: 920
• 3e Ouyang X.-H, Song R.-J, Li J.-H. Chem. Asian J. 2018; 13: 2316
• 3f Carreras J, Gopakumar G, Gu L, Gimeno A, Linowski P, Petuskova J, Thiel W, Alcarazo M. J. Am. Chem. Soc. 2013; 135: 18815
• 3g Komeyama K, Igawa R, Takaki K. Chem. Commun. 2010; 46: 1748
• 3h Mamane V, Hannen P, Fürstner A. Chem. Eur. J. 2004; 10: 4556
• 3i Fürstner A, Mamane V. J. Org. Chem. 2002; 67: 6264
• 4a McAtee CC, Riehl PS, Schindler CS. J. Am. Chem. Soc. 2017; 139: 2960
• 4b Xia Y, Qu P, Liu Z, Ge R, Xiao Q, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2013; 52: 2543
• 4c Xia Y, Liu Z, Xiao Q, Qu P, Ge R, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2012; 51: 5714
• 4d Bera K, Sarkar S, Jalal S, Jana U. J. Org. Chem. 2012; 77: 8780
• 5a Matsushima T, Kobayashi S, Watanabe S. J. Org. Chem. 2016; 81: 7799
• 5b Murai M, Hosokawa N, Roy D, Takai K. Org. Lett. 2014; 16: 4134
• 5c Iuliano A, Piccioli P, Fabbri D. Org. Lett. 2004; 6: 3711

Selected example, see:
• 6a Ozaki K, Murai K, Matsuoka W, Kawasumi K, Ito H, Itami I. Angew. Chem. Int. Ed. 2017; 56: 1361
• 6b Ozaki K, Kawasumi K, Murai K, Ito H, Itami I. Nat. Commun. 2015; 6: 6251
• 6c Frejka D, Ulč J, Kantchev EA. B, Císařová I, Kotora M. ACS Catal. 2018; 8: 10290
• 6d Yan J, Yoshikai N. Org. Lett. 2017; 19: 6630
• 6e Yang Y.-Z, Song R.-J, Li J.-H. Org. Lett. 2019; 21: 3228
• 6f Shoji Y, Tanaka N, Muranaka S, Shigeno N, Sugiyama H, Takenouchi K, Hajjaj F, Fukushima T. Nat. Commun. 2016; 7: 12704
• 6g Wu Y, Wu F, Zhu D, Luo B, Wang H, Hu Y, Wen S, Huang P. Org. Biomol. Chem. 2015; 13: 10386
• 6h Nagata T, Hirano K, Satoh T, Miura M. J. Org. Chem. 2014; 79: 8960
• 6i Lin Y.-D, Cho C.-L, Ko C.-W, Pulte A, Wu Y.-T. J. Org. Chem. 2012; 77: 9979
• 6j Korotvička A, Csařov I, Roithov J, Kotora M. Chem. Eur. J. 2012; 18: 4200
• 6k Matsumoto A, Ilies L, Nakamura E. J. Am. Chem. Soc. 2011; 133: 6557
• 6l Wang C, Rakshit S, Glorius F. J. Am. Chem. Soc. 2010; 132: 14006
• 6m Shimizu M, Nagao I, Tomioka Y, Kadowaki T, Hiyama T. Tetrahedron 2011; 67: 8014
• 6n Shimizu M, Nagao I, Tomioka Y, Hiyama T. Angew. Chem. Int. Ed. 2008; 47: 8096
• 6o Kanno K.-i, Liu Y, Iesato A, Nakajima K, Takahashi T. Org. Lett. 2005; 7: 5453
• 7a Gou B.-B, Yang H, Sun H.-R, Chen J, Wu J, Zhou L. Org. Lett. 2019; 21: 80
• 7b Iwasaki M, Araki Y, Iino S, Nishihara Y. J. Org. Chem. 2015; 80: 9247
• 7c Shimizu M, Tomioka Y, Nagao I, Kadowaki T, Hiyama T. Chem. Asian J. 2012; 7: 1644
• 7d Worlikar SA, Larock RC. J. Org. Chem. 2009; 74: 9132
• 8a Song J, Wang S, Sun H, Fan Y, Xiao K, Qian Y. Org. Biomol. Chem. 2019; 17: 3328
• 8b Iwasaki M, Araki Y, Nishihara Y. J. Org. Chem. 2017; 82: 6242
• 8c Liu Z, Larock RC. Angew. Chem. Int. Ed. 2007; 46: 2535
• 8d Catellani M, Motti E, Baratta S. Org. Lett. 2001; 3: 3611
• 8e Yoshikawa E, Yamamoto Y. Angew. Chem. Int. Ed. 2000; 39: 173
• 8f Yoshikawa E, Radhakrishnan KV, Yamamoto Y. J. Am. Chem. Soc. 2000; 122: 7280
• 8g Peña D, Pérez D, Guitián E, Castedo L. J. Am. Chem. Soc. 1999; 121: 5827
• 8h Radhakrishnan KV, Yoshikawa E, Yamamoto Y. Tetrahedron Lett. 1999; 40: 7533
• 8i Dyker G, Kellner A. Tetrahedron Lett. 1994; 35: 7633
• 9a Fu WC, Wang Z, Chan WT. K, Lin Z, Kwong FY. Angew. Chem. Int. Ed. 2017; 56: 7166
• 9b Zhao Q, Fu WC, Kwong FY. Angew. Chem. Int. Ed. 2018; 57: 3381
• 9c Fu WC, Zheng B, Zhao Q, Chan WT. K, Kwong FY. Org. Lett. 2017; 19: 4335
• 10a Domino Reactions: Concepts for Efficient Organic Synthesis. Tietze LF. Wiley-VCH; Weinheim: 2014
• 10b Domino Reactions in Organic Synthesis, 1st ed. Tietze LF, Brasche G, Gericke KM. Wiley-VCH; Weinheim: 2006

For reviews, see:
• 11a Ping Y, Li Y, Zhu J, Kong W. Angew. Chem. Int. Ed. 2019; 58: 1562
• 11b Franzoni I, Yoon H, García-López J.-A, Poblador-Bahamonde AI, Lautens M. Chem. Sci. 2018; 9: 1496
• 11c Mehta VP, García-López J.-A. ChemCatChem 2017; 9: 1149
• 11d Pérez-Gómez M, Navarro L, Saura-Llamas I, Bautista D, Lautens M, García-López J.-A. Organometallics 2017; 36: 4465

For selected reviews, see:
• 12a Liu Z.-S, Gao Q, Cheng H.-G, Zhou Q. Chem. Eur. J. 2018; 24: 15461
• 12b Della Ca’ N, Fontana M, Motti E, Catellani M. Acc. Chem. Res. 2016; 49: 1389
• 12c Ye J, Lautens M. Nat. Chem. 2015; 7: 863
• 12d Martins A, Mariampillai B, Lautens M. Top. Curr. Chem. 2009; 292: 1
• 13a Zhou B, Wu Z, Ma D, Ji X, Zhang Y. Org. Lett. 2018; 20: 6440
• 13b Zhou B, Lu A, Shao C, Liang X, Zhang Y. Chem. Commun. 2018; 54: 10598
• 13c Zhou B, Wu Z, Qi W, Sun X, Zhang Y. Adv. Synth. Catal. 2018; 360: 4480
• 13d Tian Q, Larock RC. Org. Lett. 2000; 2: 3329
• 13e Dyker G, Nerenz F, Siemsen P, Bubenitschek P, Jones PG. Chem. Ber. 1996; 129: 1265
• 14a Li W, Chen W, Zhou B, Xu Y, Deng G, Liang Y, Yang Y. Org. Lett. 2019; 21: 2718
• 14b Yang Y, Zhou B, Zhu X, Deng G, Liang Y, Yang Y. Org. Lett. 2018; 20: 5402
• 14c Xu Y, Liu X, Chen W, Deng G, Liang Y, Yang Y. J. Org. Chem. 2018; 83: 13930
• 14d Li W, Xiao G, Deng G, Liang Y. Org. Chem. Front. 2018; 5: 1488
• 14e Xiao G, Chen L, Deng G, Liu J, Liang Y. Tetrahedron Lett. 2018; 59: 1836
• 14f Luo X, Xu Y, Xiao G, Liu W, Qian C, Deng G, Song J, Liang Y, Yang C. Org. Lett. 2018; 20: 2997
• 15 Yu J, Yan H, Zhu C. Angew. Chem. Int. Ed. 2016; 55: 1143