Carbon–Carbon Bond Forming Reactions in Diazines via Transition-Metal-Catalyzed C–H Bond Activation

Abstract

An overview of the key achievements concerning C–C bond-forming processes with diazines (pyridazines, pyrimidines, and pyrazines) and benzodiazines (cinnolines, phthalazines, quinazolines, and quinoxalines) under transition-metal-catalyzed C–H activation is presented. The focus is on examples in which C–H functionalization takes place in the diazine or benzodiazine core because of the relevance of these compounds in material science and as active pharmaceutical ingredients. These metal-catalyzed protocols benefit from the biased reactivity of the C–H bonds targeted or from the presence of a rationally designed directing group proximate to the C–H bond to be functionalized. As such, innovative alkylations, alkenylations, alkynylations, arylations, and carboxylations are accomplished within such skeletons in a step- and atom-economy fashion.

1 Introduction

2 Transition-Metal-Catalyzed C–H Alkylation of Diazines

3 Transition-Metal-Catalyzed C–H Alkynylation of Diazines

4 Transition-Metal-Catalyzed C–H Alkenylation of Diazines

5 Transition-Metal-Catalyzed C–H Arylation of Diazines

6 Transition-Metal-Catalyzed C–H Carboxylation of Diazines

7 Conclusion

Key words

diazines - C–H activation - arylation - alkenylation - alkylation - metal catalyst

Publication History

Received: 22 May 2023

Accepted after revision: 20 July 2023

Accepted Manuscript online:
20 July 2023

Article published online:
12 September 2023

• References

• 1a Maes BU. W, Lemière GL. F. In Comprehensive Heterocyclic Chemistry III, Vol. 8. Katritzky AR, Ramsden CA, Scriven EF. V, Taylor RJ. K. Elsevier; Amsterdam: 2008: 1
• 1b Rewcastle GW. In Comprehensive Heterocyclic Chemistry III, Vol. 8. Katritzky AR, Ramsden CA, Scriven EF. V, Taylor RJ. K. Elsevier; Amsterdam: 2008: 117
• 1c Sato N. In Comprehensive Heterocyclic Chemistry III, Vol. 8. Katritzky AR, Ramsden CA, Scriven EF. V, Taylor RJ. K. Elsevier; Amsterdam: 2008: 273
• 1d Pozharskii AF, Sodatenkov AT, Katritzky AR. Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry, Biochemistry and Applications, 2nd ed. Wiley; Chichester: 2011
• 1e Vitaku E, Smith DT, Njardarson JT. J. Med. Chem. 2014; 57: 10257
• 1f Baumann M, Baxendale IR. Beilstein J. Org. Chem. 2013; 9: 2265
• 1g Yamaguchi J, Yamaguchi AD, Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
• 1h Vila N, Besada P, Costas T, Costas-Lago MC, Teran C. Eur. J. Med. Chem. 2015; 97: 462
• 1i Sergeev PV, Nenajdenko VG. Russ. Chem. Rev. 2020; 89: 393
• 2a Itami K, Yamazaki D, Yoshida J.-I. J. Am. Chem. Soc. 2004; 126: 15396
• 2b Achelle S, Plé N. Curr. Org. Synth. 2012; 9: 163
• 2c Achelle S, Baudequin C. In Targets in Heterocyclic Systems, Vol. 17. Attanasi OA, Spinelli D. Soc. Chim. Italiana; Roma: 2013: 1
• 2d Ortiz RP, Casado J, Hernandez V, Lopez Navarrete JT, Letizia JA, Ratner MA, Facchetti A, Marks TJ. Chem. Eur. J. 2009; 15: 5023
• 3a Verbitskiy EV, Rusinov GL, Chupakhin ON, Charushin VN. Synthesis 2018; 50: 193
• 3b Charushin VN, Chupakhin ON. Pure Appl. Chem. 2004; 76: 1621
• 3c Chupakhin ON, Charushin VN. Tetrahedron Lett. 2016; 57: 2665
• 4a Duncton MA. J. MedChemComm 2011; 2: 1135
• 4b Proctor RS. J, Phipps RJ. Angew. Chem. Int. Ed. 2019; 58: 13666
• 4c Yanagisawa S, Ueda K, Taniguchi T, Itami K. Org. Lett. 2008; 10: 4673
• 4d Thatikonda T, Singh U, Ambala S, Vishwakarma RA, Singh PP. Org. Biomol. Chem. 2016; 14: 4312
• 4e Ambala S, Thatikonda T, Sharma S, Munagala G, Yempalla KR, Vishwakarma RA, Singh PP. Org. Biomol. Chem. 2015; 13: 11341
• 4f Seiple IB, Su S, Rodriguez RA, Gianatassio R, Fujiwara Y, Sobel AL, Baran PS. J. Am. Chem. Soc. 2010; 132: 13194
• 5a Chevallier F, Mongin F. Chem. Soc. Rev. 2008; 37: 595
• 5b Seggio A, Chevallier F, Vaultier M, Mongin F. J. Org. Chem. 2007; 72: 6602
• 5c Balkenhohl M, Knochel P. SynOpen 2018; 2: 78
• 5d Groll K, Manolikakes SM, du Jourdin XM, Jaric M, Bredihhin A, Karaghiosoff K, Carell T, Knochel P. Angew. Chem. Int. Ed. 2013; 52: 6776
• 5e Rossi R, Lessi M, Manzini C, Marianetti G, Bellina F. Adv. Synth. Catal. 2015; 357: 3777

Selected representative examples:
• 6a Wimmer L, Rycek L, Koley M, Schnürch M. Top. Heterocycl. Chem. 2014; 45: 61
• 6b Maes BU. W, Tapolcsanyi P, Meuers C, Matyus M. Curr. Org. Chem. 2006; 10: 377
• 6c Guram AS, King AO, Allen JG, Wang X, Schenkel LB, Chan J, Bunel EE, Faul MM, Larsen RD, Martinelli MJ, Reider PJ. Org. Lett. 2006; 8: 1787
• 6d Lee D.-H, Jung J.-Y, Jin M.-J. Green Chem. 2010; 12: 2024
• 6e Stanetty P, Hattinger G, Schnürch M, Mihovilovic MD. J. Org. Chem. 2005; 70: 5215
• 6f Beneritter P, de Araujo-Junior JX, Schmitt M, Bourguignon J.-J. Tetrahedron 2007; 63: 12465
• 6g Fürstner A, Letner A, Mendez M, Krause H. J. Am. Chem. Soc. 2002; 124: 13856
• 7a Gensch T, Hopkinson MN, Glorius F, Wencel-Delord J. Chem. Soc. Rev. 2016; 45: 2900
• 7b Sambiagio C, Schönbauer D, Blieck R, Dao-Huy T, Pototschnig G, Schaaf P, Wiesinger T, Zia MF, Wencel-Delord J, Besset T, Maes BU. W, Schnürch M. Chem. Soc. Rev. 2018; 47: 6603
• 7c Hartwig JF, Larsen MA. ACS Cent. Sci. 2016; 2: 281
• 7d Rogge T, Kaplaneris N, Chatani N, Kim J, Chang S, Punji B, Schafer LL, Musaev DG, Wencel-Delord J, Roberts CA, Sarpong R, Wilson ZE, Brimble MA, Johansson MJ, Ackermann L. Nat. Rev. Methods Primers 2021; 1: 43
• 7e Gandeepan P, Müller T, Zell D, Cera G, Warratz S, Ackermann L. Chem. Rev. 2019; 119: 2192
• 7f Gandeepan P, Finger LH, Meyer TH, Ackermann L. Chem. Soc. Rev. 2020; 49: 4254
• 7g Loup J, Dhawa U, Pesciaioli F, Wencel-Delord J, Ackermann L. Angew. Chem. Int. Ed. 2019; 58: 12803
• 7h Rossi R, Lessi M, Manzini C, Marianetti G, Bellina F. Tetrahedron 2016; 72: 1795
• 7i Théveau L, Schneider C, Fruit C, Hoarau C. ChemCatChem 2016; 8: 3183
• 7j Rossi R, Ciofalo M. Curr. Org. Chem. 2022; 26: 215
• 7k Murakami K, Yamada S, Kaneda T, Itami K. Chem. Rev. 2017; 117: 9302
• 8 Tran G, Hesp KD, Mascitti V, Ellman JA. Angew. Chem. Int. Ed. 2017; 56: 5899
• 9a Wiedemann SH, Ellman JA, Bergman RG. J. Org. Chem. 2006; 71: 1969
• 9b Wiedemann SH, Lewis JC, Ellman JA, Bergman RG. J. Am. Chem. Soc. 2006; 128: 2452
• 10 Gribble MW. Jr, Guo S, Buchwald SL. J. Am. Chem. Soc. 2018; 140: 5057
• 11a Catellani M, Frignani F, Rangoni A. Angew. Chem. Int. Ed. Engl. 1997; 36: 119
• 11b Wang J, Dong G. Chem. Rev. 2019; 119: 7478
• 11c Lautens M, Piguel S. Angew. Chem. Int. Ed. 2000; 39: 1045
• 12 Gao Q, Shang Y, Song F, Ye J, Liu Z.-S, Li L, Cheng H.-G, Zhou Q. J. Am. Chem. Soc. 2019; 141: 15986
• 13 Dong Z, Lu G, Wang J, Liu P, Dong G. J. Am. Chem. Soc. 2018; 140: 8551
• 14 Wang X, Zhao S, Liu J, Zhu D, Guo M, Tang X, Wang G. Org. Lett. 2017; 19: 4187
• 15 Zhang S, Weniger F, Kreyenschulte CR, Lund H, Bartling S, Neumann H, Ellinger S, Taeschler C, Beller M. Catal. Sci. Technol. 2020; 10: 1731
• 16 Yi J, Yang L, Xia C, Li F. J. Org. Chem. 2015; 80: 6213
• 17 Liu Y.-J, Liu Y.-H, Yin X.-S, Gu W.-J, Shi B.-F. Chem. Eur. J. 2015; 21: 205
• 18 Ye M, Gao G.-L, Yu J.-Q. J. Am. Chem. Soc. 2011; 133: 6964
• 19 Cong X, Tang H, Wu C, Zeng X. Organometallics 2013; 32: 6565
• 20 Das A, Jana A, Maji B. Chem. Commun. 2020; 56: 4284
• 21 Wen P, Li Y, Zhou K, Ma C, Lan X, Ma C, Huang G. Adv. Synth. Catal. 2012; 354: 2135
• 22 Zhang Z, Tanaka K, Yu J.-Q. Nature 2017; 543: 538
• 23 Yin B, Fu M, Wang L, Liu J, Zhu Q. Chem. Commun. 2020; 56: 3293
• 24 Zhang Z, Zheng Y, Sun Z, Dai Z, Tang Z, Ma J, Ma C. Adv. Synth. Catal. 2017; 359: 2259
• 25 Zhou J, Li B, Qian Z.-C, Shi B.-F. Adv. Synth. Catal. 2014; 356: 1038
• 26 Cai S, Chen C, Shao P, Xi C. Org. Lett. 2014; 16: 3142
• 27 Nakao Y, Kanyiva KS, Hiyama T. J. Am. Chem. Soc. 2008; 130: 2448
• 28 Wang C.-S, Di Monaco S, Thai AN, Rahman MS, Pang BP, Wang C, Yoshikai N. J. Am. Chem. Soc. 2020; 142: 12878
• 29 Morioka R, Nobushige K, Satoh T, Hirano K, Miura M. Org. Lett. 2015; 17: 3130
• 30 Karak P, Dutta C, Dutta T, Koner AL, Choudhury J. Chem. Commun. 2019; 55: 6791
• 31 Meesa SR, Naikawadi PK, Gugulothu K, Kumar KS. Org. Biomol. Chem. 2020; 18: 3032
• 32 Yang Y, Lan J, You J. Chem. Rev. 2017; 117: 8787
• 33 Liu B, Huang Y, Lan J, Song F, You J. Chem. Sci. 2013; 4: 2163
• 34 Ren X, Wen P, Shi X, Wang Y, Li J, Yang S, Yan H, Huang G. Org. Lett. 2013; 15: 5194
• 35 Yamada S, Kaneda T, Steib P, Murakami K, Itami K. Angew. Chem. Int. Ed. 2019; 58: 8341
• 36 Chen C, Chen X, Zhao H, Jiang H, Zhang M. Org. Lett. 2017; 19: 3390
• 37a Campeau L.-C, Fagnou K. Chem. Commun. 2006; 1253
• 37b Alberico D, Scott ME, Lautens M. Chem. Rev. 2007; 107: 174
• 37c Seregin IV, Gevorgyan V. Chem. Soc. Rev. 2007; 36: 1173
• 37d Ackermann L. Synlett 2007; 507
• 37e Lewis JC, Bergman RG, Ellman JA. Acc. Chem. Res. 2008; 41: 1013
• 37f Arockiam PB, Bruneau C, Dixneuf PH. Chem. Rev. 2012; 112: 5879
• 37g Hussain I, Singh T. Adv. Synth. Catal. 2014; 356: 1661
• 38 Do H.-Q, Khan RM. K, Daugulis O. J. Am. Chem. Soc. 2008; 130: 15185
• 39 Do H.-Q, Daugulis O. J. Am. Chem. Soc. 2009; 131: 17052
• 40 Truong T, Alvarado J, Tran LD, Daugulis O. Org. Lett. 2010; 12: 1200
• 41a Tobisu M, Hyodo I, Chatani N. J. Am. Chem. Soc. 2009; 131: 12070
• 41b Hyodo I, Tobisu M, Chatani N. Chem. Asian J. 2012; 7: 1357
• 42a Berman AM, Bergman RG, Ellman JA. J. Org. Chem. 2010; 75: 7863
• 42b Lewis JC, Wiedemann SH, Bergman RG, Ellman JA. Org. Lett. 2004; 6: 35
• 42c Lewis JC, Wu JY, Bergman RG, Ellman JA. Angew. Chem. Int. Ed. 2006; 45: 1589
• 43 Kwak J, Kim M, Chang S. J. Am. Chem. Soc. 2011; 133: 3780
• 44 Guchhait SK, Kandekar S, Kashyap M, Taxak N, Bharatam PV. J. Org. Chem. 2012; 77: 8321
• 45 Nguyen Q.-H, Guo S.-M, Royal T, Baudoin O, Cramer N. J. Am. Chem. Soc. 2020; 142: 2161
• 46 Zhang J, Parker TC, Chen W, Williams L, Khrustalev VN, Jucov EV, Barlow S, Timofeeva TV, Marder SR. J. Org. Chem. 2016; 81: 360
• 47 Wei D, Li M.-Y, Zhu B.-B, Yang X.-D, Fang Z, Feng C.-G, Lin G.-Q. Angew. Chem. Int. Ed. 2019; 58: 16543
• 48 Shi H, Lu Y, Weng J, Bay KL, Chen X, Tanaka K, Verma P, Houk KN, Yu J.-Q. Nat. Chem. 2020; 12: 399
• 49 Basolo L, Beccalli EM, Borsini E, Broggini G. Tetrahedron 2009; 65: 3486
• 50 Zhao Y, Snieckus V. Adv. Synth. Catal. 2014; 356: 1527
• 51 Sirois JJ, Davis R, DeBoef B. Org. Lett. 2014; 16: 868
• 52 Zhu C, Oliveira JC. A, Shen Z, Huang H, Ackermann L. ACS Catal. 2018; 8: 4402
• 53 Johnston AJ. S, Ling KB, Sale D, Lebrasseur N, Larrosa I. Org. Lett. 2016; 18: 6094
• 54 Srinivasan R, Dey A, Nagarajan NS, Kumaran RS, Gandhi T, Maiti D. Chem. Commun. 2017; 53: 11709
• 55 Wisniewski SR, Stevens JM, Yu M. J. Org. Chem. 2019; 84: 4704
• 56 Wisniewski SR, Savage SA, Romero EO. J. Org. Chem. 2019; 84: 7961
• 57 Boogaerts II. F, Nolan SP. J. Am. Chem. Soc. 2010; 132: 8858
• 58 Gramage-Doria R, Achelle S, Bruneau C, Robin-le Guen F, Dorcet V, Roisnel T. J. Org. Chem. 2018; 83: 1462
• 59 Stefane B, Brodnik Zugelj HB, Groselj U, Kuzman P, Svete J, Pozgan F. Eur. J. Org. Chem. 2017; 1855
• 60 Kuzman P, Pozgan F, Meden A, Svete J, Stefane B. ChemCatChem 2017; 9: 3380
• 61 Hrovat S, Drev M, Grošelj U, Perdih F, Svete J, Štefane B, Požgan F. Catalysts 2020; 10: 421
• 62 Drev M, Grošelj U, Ledinek B, Perdih F, Svete J, Štefane B, Požgan F. ChemCatChem 2018; 10: 3824
• 63 Štefane B, Fabris J, Požgan F. Eur. J. Org. Chem. 2011; 3474
• 64 Benzai A, Derridj F, Doucet H, Soulé J.-F. ChemCatChem 2021; 13: 338
• 65 Idris I, Derridj F, Roisnel T, Doucet H, Soulé J.-F. New J. Chem. 2018; 42: 16036
• 66 Lakshman MK, Deb AC, Chamala RR, Pradhan P, Pratap R. Angew. Chem. Int. Ed. 2011; 50: 11400
• 67 Guo H.-M, Jiang L.-L, Niu H.-Y, Rao W.-H, Liang L, Mao R.-Z, Li D.-Y, Qu G.-R. Org. Lett. 2011; 13: 2008
• 68 Wang L, Xiong D, Jie L, Yu C, Cui X. Chin. Chem. Lett. 2018; 29: 907
• 69 Leitch JA, Heron CJ, McKnight J, Kociok-Köhn G, Bhonoahd Y, Frost CG. Chem. Commun. 2017; 53: 13039
• 70 Bag S, Jayarajan R, Mondal R, Maiti D. Angew. Chem. Int. Ed. 2017; 56: 3182
• 71 Jayarajan R, Das J, Bag S, Chowdhury R, Maiti D. Angew. Chem. Int. Ed. 2018; 57: 7659
• 72 Achar TK, Zhang X, Mondal R, Shanavas MS, Maiti S, Maity S, Pal N, Paton RS, Maiti D. Angew. Chem. Int. Ed. 2019; 58: 10353
• 73 Bag S, Surya K, Mondal A, Jayarajan R, Dutta U, Porey S, Sunoj RB, Maiti D. J. Am. Chem. Soc. 2020; 142: 12453
• 74 Brochetta M, Borsari T, Bag S, Jana S, Maiti S, Porta A, Werz DB, Zanoni G, Maiti D. Chem. Eur. J. 2019; 25: 10323
• 75 Gramage-Doria R, Bruneau C. Coord. Chem. Rev. 2021; 428: 21362