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Synthesis 2022; 54(15): 3328-3340
DOI: 10.1055/a-1816-3334
DOI: 10.1055/a-1816-3334
short review
Catalyst Engineering through Heterobidentate (N–X-Type) Ligand Design for Iridium-Catalyzed Borylation
This work was supported by grants from the Science and Engineering Research Board – Core Research Grant (SERB-CRG; CRG/2018/000133), Science and Engineering Research Board – Scientific and Useful Profound Research Advancement (SERB-SUPRA; SPR/2019/000158), and Science and Engineering Research Board – Science and Technology Award for Research (SERB-STAR; STR/2019/000045). M.E.H. thanks SERB-SUPRA for an RA fellowship, M.M.M.H. thanks the University Grants Commission (UGC) for an SRF, C.H. thanks Council of Scientific and Industrial Research (CSIR) for an SRF, S.D. and S.G. thanks the CSIR for a JRF fellowship, J.C. thanks UGC for an SRF. B.C. thanks SERB-STAR for an award.
Abstract
Iridium-catalyzed C–H activation and borylation reactions operate under mild conditions that enable easy and atom-economical installation of the versatile boronate ester group in (het)arenes and alkanes. The standard catalytic system for iridium-catalyzed borylation uses [Ir(cod)(OMe)]2 as a precatalyst, a bipyridine type ligand, and B2pin2 or HBpin as the borylating agent. Initially, a bipyridine-ligated trisboryl–iridium complex is generated that enables the borylation reaction and the regioselectivity is mainly governed by the sterics of substituents present on the ring. As a result, monosubstituted and 1,2-disubstituted arenes give mixtures of isomers. Significant efforts by several research groups have overcome the selectivity issue for directed proximal C–H borylation by introducing a directing group and newly developed ligands. This short review aims to summarize recent elegant discoveries in directed C(sp2)–H and C(sp3)–H borylation by using heterobidentate ligand (P/N–Si, N–B, and N–C) coordinated iridium catalysts.
1 Introduction
2 Iridium-Catalyzed Directed C–H Borylation of C(sp2)–H Bonds
3 Iridium-Catalyzed Directed C–H Borylation of C(sp3)–H Bonds
4 Conclusions
Key words
C–H bond activation - ligand development - directing groups - heterobidentate ligand - iridium catalystPublikationsverlauf
Eingereicht: 07. März 2022
Angenommen nach Revision: 04. April 2022
Accepted Manuscript online:
04. April 2022
Artikel online veröffentlicht:
16. Mai 2022
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References
- 1a Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
- 1b Daugulis O, Do H.-Q, Shabashov D. Acc. Chem. Res. 2009; 42: 1074
- 1c Mkhalid IA. I, Barnard JH, Marder TB, Murphy JM, Hartwig JF. Chem. Rev. 2010; 110: 890
- 1d Leow D, Li G, Mei T.-S, Yu J.-Q. Nature 2012; 486: 518
- 1e Engle KM, Mei T.-S, Wasa M, Yu J.-Q. Acc. Chem. Res. 2012; 45: 788
- 1f Murai S, Kakiuchi F, Sekine S, Tanaka Y, Kamatani A, Sonoda M, Chatani N. Nature 1993; 366: 529
- 1g Cheng C, Hartwig JF. Science 2014; 343: 853
- 1h Gensch T, Hopkinson MN, Glorius F, Wencel-Delord J. Chem. Soc. Rev. 2016; 45: 2900
- 1i Wang P, Verma P, Xia G, Shi J, Qiao JX, Tao S, Cheng PT. W, Poss MA, Farmer ME, Yeung K.-S, Yu J.-Q. Nature 2017; 551: 489
- 1j Sambiagio C, Schönbauer D, Blieck R, Dao-Huy T, Pototschnig G, Schaaf P, Wiesinger T, Farooq ZiaM, Wencel-Delord J, Besset T, Maes BU. W, Schnürch M. Chem. Soc. Rev. 2018; 47: 6603
- 1k Sinha SK, Guin S, Maiti S, Biswas JP, Porey S, Maiti D. Chem. Rev. 2022; 122: 5682
- 1l Li B, Ali AI. M, Ge H. Chem 2020; 6: 2591
- 1m Dalton T, Faber T, Glorius F. ACS Cent. Sci. 2021; 7: 245
- 2 Shilov AE, Shul’pin GB. Chem. Rev. 1997; 97: 2879
- 3 Snieckus V. Chem. Rev. 1990; 90: 879
- 4a Cho J.-Y, Tse MK, Holmes D, Maleczka RE. Jr, Smith MR. III. Science 2002; 295: 305
- 4b Ishiyama T, Takagi J, Ishida K, Miyaura N, Anasrasi NR, Hartwig JF. J. Am. Chem. Soc. 2002; 124: 390
- 4c Ishiyama T, Takagi J, Hartwig JF, Miyaura N. Angew. Chem. Int. Ed. 2002; 41: 3056
- 4d Tian Y.-M, Guo X.-N, Braunschweig H, Radius U, Marder TB. Chem. Rev. 2021; 121: 3561
- 4e Wang M, Shi Z. Chem. Rev. 2020; 120: 7348
- 4f Hu J, Ferger M, Shi Z, Marder TB. Chem. Soc. Rev. 2021; 50: 13129
- 4g Ramadoss B, Jin Y, Asako S, Ilies L. Science 2022; 375: 658
- 4h Wright JS, Scott PJ. H, Steel PG. Angew. Chem. Int. Ed. 2021; 60: 2796
- 5 Cross-Coupling Reactions Of Organoboranes: An Easy Way To Construct C–C Bonds (Nobel Lecture): Suzuki A. Angew. Chem. Int. Ed. 2011; 50: 6722
- 6 Miyaura N, Suzuki A. J. Chem. Soc., Chem. Commun. 1979; 866
- 7 Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
- 8 Hall DG. Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine. Wiley-VCH; Weinheim: 2005
- 9 Lawson JR, Melen RL. Organomet. Chem. 2017; 41: 1
- 10a Berkessel A, Gröger H. Asymmetric Organocatalysis . Wiley-VCH; Weinheim: 2005
- 10b Dimitrijević E, Taylor MS. ACS Catal. 2013; 3: 945
- 11 Das BC, Thapa P, Karki R, Schinke C, Das S, Kambhampati S, Banerjee SK, Veldhuizen PV, Verma A, Weiss LM, Evans T. Future Med. Chem. 2013; 5: 653
- 12 Pelter A, Smith K, Buss D, Jin Z. Heteroat. Chem. 1992; 3: 275
- 13a Ishiyama T, Murata M, Miyaura N. J. Org. Chem. 1995; 60: 7508
- 13b Murata M, Oyama T, Watanabe S, Masuda Y. J. Org. Chem. 2000; 65: 164
- 14 Iverson CN, Smith MR. III. J. Am. Chem. Soc. 1999; 121: 7696
- 15 Boller TM, Murphy JM, Hapke M, Ishiyama T, Miyaura N, Hartwig JF. J. Am. Chem. Soc. 2005; 127: 4263
- 16a Ros A, Fernandez R, Lassaletta JM. Chem. Soc. Rev. 2014; 43: 3229
- 16b Xu L, Wang G, Zhang S, Wang H, Wang L, Liu L, Jiao J, Li P. Tetrahedron 2017; 73: 7123
- 16c Haldar C, Hoque ME, Bisht R, Chattopadhyay B. Tetrahedron Lett. 2018; 59: 1269
- 16d Wright JS, Scott PJ. H, Steel PG. Angew. Chem. Int. Ed. 2020; 59: 2
- 16e Hartwig JF. Chem. Soc. Rev. 2011; 40: 1992
- 16f Hassan MM. M, Hoque ME, Dey S, Guria S, Roy B, Chattopadhyay B. Synthesis 2021; 53: 3333
- 16g Hassan MM. M, Mondal B, Singh S, Haldar C, Chaturvedi J, Bisht R, Sunoj RB, Chattopadhyay B. J. Org. Chem. 2022; 87: 4360
- 16h Miller SL, Chotana GA, Fritz JA, Chattopadhyay B, Maleczka RE. Jr, Smith MR. III. Org. Lett. 2019; 21: 6388
- 17 Boebel TA, Hartwig JF. J. Am. Chem. Soc. 2008; 130: 7534
- 18a Robbins DW, Boebel TA, Hartwig JF. J. Am. Chem. Soc. 2010; 132: 4068
- 18b Larsen MA, Cho SH, Hartwig JF. J. Am. Chem. Soc. 2016; 138: 762
- 18c Su B, Hartwig JF. Angew. Chem. Int. Ed. 2018; 57: 10163
- 18d Cho SH, Hartwig JF. J. Am. Chem. Soc. 2013; 135: 8157
- 19a Ishiyama T, Isou H, Kikuchi T, Miyaura N. Chem. Commun. 2010; 46: 159
- 19b Itoh H, Kikuchi T, Ishiyama T, Miyaura N. Chem. Lett. 2011; 40: 1007
- 20a Kawamorita S, Ohmiya H, Hara K, Fukuoka A, Sawamura M. J. Am. Chem. Soc. 2009; 131: 5058
- 20b Yamazaki K, Kawamorita S, Ohmiya H, Sawamura M. Org. Lett. 2010; 12: 3978
- 20c Kawamorita S, Miyazaki T, Ohmiya H, Iwai T, Sawamura M. J. Am. Chem. Soc. 2011; 133: 19310
- 21a Ros A, Estepa B, López-Rodríguez R, Álvarez E, Fernández R, Lassaletta JM. Angew. Chem. Int. Ed. 2011; 50: 11724
- 21b Ros A, López-Rodríguez R, Estepa B, Álvarez E, Fernández R, Lassaletta JM. J. Am. Chem. Soc. 2012; 134: 4573
- 21c López-Rodríguez R, Ros A, Fernández R, Lassaletta JM. J. Org. Chem. 2012; 77: 9915
- 22 Roering AJ, Hale LV. A, Squier PA, Ringgold MA, Wiederspan ER, Clark TB. Org. Lett. 2012; 14: 3558
- 23a Kuninobu Y, Ida H, Nishi M, Kanai M. Nat. Chem. 2015; 7: 712
- 23b Lu X, Yoshigoe Y, Ida H, Nishi M, Kanai M, Kuninobu Y. ACS Catal. 2019; 9: 1705
- 23c Wang J, Torigoe T, Kuninobu Y. Org. Lett. 2019; 21: 1342
- 24a Saito Y, Segawa Y, Itami K. J. Am. Chem. Soc. 2015; 137: 5193
- 24b Saito Y, Yamanoue K, Segawa Y, Itami K. Chem 2020; 6: 985
- 25a Bisht R, Chattopadhyay B. J. Am. Chem. Soc. 2016; 138: 84
- 25b Bisht R, Chattopadhyay B. Synlett 2016; 27: 2043
- 25c Hoque ME, Bisht R, Haldar C, Chattopadhyay B. J. Am. Chem. Soc. 2017; 139: 7745
- 25d Bisht R, Hoque ME, Chattopadhyay B. Angew. Chem. Int. Ed. 2018; 57: 15762
- 25e Chaturvedi J, Haldar C, Bisht R, Pandey G, Chattopadhyay B. J. Am. Chem. Soc. 2021; 143: 7604
- 25f Chaturvedi J, Haldar C, Chattopadhyay B. Synlett 2022; 33: in press
- 25g Haldar C, Hoque EM, Chaturvedi J, Hassan MM. M, Chattopadhyay B. Chem. Commun. 2021; 57: 13059
- 26a Davis HJ, Mihai MT, Phipps RJ. J. Am. Chem. Soc. 2016; 138: 12759
- 26b Davis HJ, Genow GR, Phipps RJ. Angew. Chem. Int. Ed. 2017; 56: 13351
- 26c Mihai MT, Davis HJ, Genov GR, Phipps RJ. ACS Catal. 2018; 8: 3764
- 26d Genov GR, Douthwaite JL, Lahdenperä AS. K, Gibson DC, Phipps RJ. Science 2020; 367: 1246
- 26e Mihai MT, Williams BD, Phipps RJ. J. Am. Chem. Soc. 2019; 141: 15477
- 27 Montero Bastidas JR, Oleskey TJ, Miller SL, Smith MR. III, Maleczka RE. Jr. J. Am. Chem. Soc. 2019; 141: 15483
- 28a Yang L, Semba K, Nakao Y. Angew. Chem. Int. Ed. 2017; 56: 4853
- 28b Yang L, Uemura N, Nakao Y. J. Am. Chem. Soc. 2019; 141: 7972
- 29 Reyes RL, Sato M, Iwai T, Suzuki K, Maeda S, Sawamura M. Science 2020; 369: 970
- 30 Fang H, Choe Y.-K, Li Y, Shimada S. Chem. Asian J. 2011; 6: 2512
- 31 Ghaffari B, Preshlock SM, Plattner DL, Staples RJ, Maligres PE, Krska SW, Maleczka RE. Jr, Smith MR. III. J. Am. Chem. Soc. 2014; 136: 14345
- 32 Segawa Y, Yamashita M, Nozaki K. J. Am. Chem. Soc. 2009; 131: 9201
- 33 Spokoyny AM, Reuter MG, Stern CL, Ratner MA, Seideman T, Mirkin CA. J. Am. Chem. Soc. 2009; 131: 9482
- 34a Ogawa H, Yamashita M. Dalton Trans. 2013; 42: 625
- 34b Lin T.-P, Peters JC. J. Am. Chem. Soc. 2014; 136: 13672
- 35 Wang G, Xu L, Li P. J. Am. Chem. Soc. 2015; 137: 8058
- 36 Preshlock SM, Ghaffari B, Maligres PE, Krska SW, Maleczka RE, Smith MR. J. Am. Chem. Soc. 2013; 135: 7572
- 37 Wang G, Liu L, Wang H, Ding Y.-S, Zhou J, Mao S, Li P. J. Am. Chem. Soc. 2017; 139: 91
- 38 Zou X, Zhao H, Li Y, Gao Q, Ke Z, Xu S. J. Am. Chem. Soc. 2019; 141: 5334
- 39 Saint-Denis TG, Zhu R.-Y, Chen G, Wu Q.-F, Yu J.-Q. Science 2018; 359: 759
- 40 Jiao J, Nie W, Song P, Li P. Org. Biomol. Chem. 2021; 19: 355
- 41 Liu L, Wang G, Jiao J, Li P. Org. Lett. 2017; 19: 6132
- 42 Hoque ME, Hassan MM. M, Chattopadhyay B. J. Am. Chem. Soc. 2021; 143: 5022
- 43 Shen K, Fu Y, Li J, Liu L, Guo Q. Tetrahedron 2007; 63: 1568
- 44 Song P, Hu L, Yu T, Jiao J, He Y, Xu L, Li P. ACS Catal. 2021; 11: 7339
- 45 Hyland SN, Meck EA, Tortosa M, Clark TB. Tetrahedron Lett. 2019; 60: 1096
- 46 Kawamorita S, Miyazaki T, Iwai T, Ohmiya H, Sawamura M. J. Am. Chem. Soc. 2012; 134: 12924
- 47 Shi Y, Gao Q, Xu S. J. Am. Chem. Soc. 2019; 141: 10599
- 48 Chen L, Yang Y, Liu L, Gao Q, Xu S. J. Am. Chem. Soc. 2020; 142: 12062
- 49 Yang Y, Chen L, Xu S. Angew. Chem. Int. Ed. 2021; 60: 3524
- 50 Du R, Liu L, Xu S. Angew. Chem. Int. Ed. 2021; 60: 5843
- 51a Kawamorita S, Murakami R, Iwai T, Sawamura M. J. Am. Chem. Soc. 2013; 135: 2947
- 51b Iwai T, Murakami R, Harada T, Kawamorita S, Sawamura M. Adv. Synth. Catal. 2014; 356: 1563