Boronic Acids and Their Derivatives as Continuous-Flow-Friendly Alkyl Radical Precursors

Monica Oliva; Viktoriia V. Chernobrovkina; Erik V. Van der Eycken; Upendra Kumar Sharma

doi:10.1055/a-2068-6038

Synlett, Inhaltsverzeichnis

Synlett 2023; 34(14): 1662-1677
DOI: 10.1055/a-2068-6038

account

Published as part of the Special Section 13th EuCheMS Organic Division Young Investigator Workshop

Boronic Acids and Their Derivatives as Continuous-Flow-Friendly Alkyl Radical Precursors

Monica Oliva

^aLaboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001 Leuven, Belgium

,

Viktoriia V. Chernobrovkina

^bPeoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya street 6, 117198 Moscow, Russia

,

Erik V. Van der Eycken

^aLaboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001 Leuven, Belgium

^bPeoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya street 6, 117198 Moscow, Russia

,

Upendra Kumar Sharma ∗

^aLaboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, 3001 Leuven, Belgium

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

Since its recognition as an enabling tool to form challenging C–C and C–heteroatom bonds under mild and sustainable conditions, photoredox catalysis has been in the spotlight within the synthetic community. As a consequence, the interest in developing novel synthetic strategies has spiked together with the need to define suitable technologies to overcome scale-up issues dictated by the Bouguer–Beer–Lambert law. In this context, continuous-flow reactors play a major role in increasing the efficiency of a given photocatalyzed reaction, thus rendering scale-up processes more accessible. In the alkyl radical precursor landscape, boron-based species have begun to play a predominant role. Though the reactivity of trifluoroborates has been deeply investigated, the interest in using other boron species as radical precursors in photocatalyzed reactions has recently arisen. This late exploration lies in the fact that the high oxidation potential of boronic acids (BAs) hinders their possible applications. Nevertheless, to circumvent this issue, a diverse array of activation modes has been developed, exploiting in most cases the inherent Lewis acidity of the boronic acid. The aim of this Account is to highlight our recent contribution to this vibrant field with a focus on broad applicability, selectivity, and scalability via continuous-flow methodology. For the sake of clarity, the Account is discussed under the following sections.

1 Introduction

2 Why Photochemistry in Flow?

2.1 Preliminary Considerations

2.2 Batch vs. Flow Photochemical Reactions

2.3 Commercially Available Lab-Scale Solutions for Photoflow Chemistry

3 Organoboron Compounds

3.1 The Evolution of Organoboron Compounds as Radical Precursors in Photoredox Catalysis

3.2 Organoboron Compounds in Flow

4 Activation of Boronic Acids towards Radical Formation

4.1 Giese-Type Addition

4.2 Petasis Reaction

4.3 Light-Driven Four-Component Reaction

4.4 Minisci Reaction

5 Conclusion and Future Perspective

Key words

photoredox catalysis - continuous-flow chemistry - boronic acid - free radicals

Volltext

Referenzen

References

1a Walling C. Tetrahedron 1985; 41: 3887
1b Ingold KU. Pure Appl. Chem. 1997; 69: 241

2 Kolbe H. Ann. Chem. Pharm. 1848; 64: 339

For selected general reviews of radical chemistry, see:

3a Free Radicals: Dynamics of Elementary Processes, Vol. 1 . Kochi JK. Wiley-Interscience; New York: 1973
3b Curran DP. Synthesis 1988; 6: 417
3c Curran DP. Synthesis 1988; 7: 489
3d Jasperse CP, Curran DP, Fevig TL. Chem. Rev. 1991; 91: 1237
3e Radicals in Organic Synthesis . Renaud P, Sibi M. Wiley-VCH; Weinheim: 2001
3f Togo H. Advanced Free Radical Reactions for Organic Synthesis. Elsevier; Amsterdam: 2003
3g Zard SZ. Radical Reactions in Organic Synthesis . Oxford University Press; Oxford: 2003

4 Kuivila HG, Menapace LW. J. Org. Chem. 1963; 28: 2165
5 Baguley PA, Walton JC. Angew. Chem. Int. Ed. 1998; 37: 3072

6a Barton DH. R, Beaton JM, Geller LE, Pechet MM. J. Am. Chem. Soc. 1960; 82: 2640
6b Barton DH. R, Beaton JM. J. Am. Chem. Soc. 1960; 82: 2641
6c Barton DH. R, Beaton JM, Geller LE, Pechet MM. J. Am. Chem. Soc. 1961; 83: 4076

Also see:

6d Walling C, Padwa A. J. Am. Chem. Soc. 1961; 83: 2207

7 Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322
8 Kalyanasundaram K. Coord. Chem. Rev. 1982; 46: 159
9 Juris A, Balzani V, Barigelletti F, Campagna S, Belser P, von Zelewsky A. Coord. Chem. Rev. 1988; 84: 85

For selected reviews, see:

10a Shaw MH, Twilton J, MacMillan DW. C. J. Org. Chem. 2016; 81: 6898
10b Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075

11 Donnelly K, Baumann M. J. Flow Chem. 2021; 11: 223

12a Lu H, Schmidt MA, Jensen KF. Lab Chip 2001; 1: 22
12b Ueno K, Kitagawa F, Kitamura N. Lab Chip 2002; 2: 231

13a Feehs RH. US3554887A, 1971
13b Doede CM, Walker CA. Chem. Eng. 1955; 62: 159

14a Pistorius A, DeGrip W. In Encyclopedia of Spectroscopy and Spectrometry, 2^nd ed. . Lindon J, Tranter G, Koppenaal D. Academic Press; Amsterdam: 2010: 142-152
14b Rodger A, Sanders K. In Encyclopedia of Spectroscopy and Spectrometry, 2^nd ed. . Lindon J, Tranter G, Koppenaal D. Academic Press; Amsterdam: 2010: 166-173
14c Mayerhöfer T, Mutschke H, Popp J. ChemPhysChem 2016; 17: 1948
14d Mayerhöfer T, Popp J. ChemPhysChem 2019; 20: 511

15a Buglioni L, Raymenants F, Slattery A, Zondag SD. A, Noël T. Chem. Rev. 2022; 122: 2752
15b Cambié D, Bottecchia C, Straathof NJ. W, Hessel V, Noël T. Chem. Rev. 2016; 116: 10276

16 Dong Z, Wen Z, Zhao F, Kuhn S, Noël T. Chem. Eng. Sci.: X 2021; 10: 100097
17 Pitzer L, Schäfer F, Glorius F. Angew. Chem. Int. Ed. 2019; 58: 8572

Selected protocols:

18a Britton J, Jamison TF. Nat. Protoc. 2017; 12: 2423
18b Straathof NJ. W, Su Y, Hessel V, Noël T. Nat. Protoc. 2016; 11: 10
18c Hone CA, Kappe CO. Chem. Methods 2021; 1: 1

19 Sender M, Ziegenbalg S. Chem. Ing. Tech. 2017; 89: 1159
20 Chemistry of the Non-Metals . Steudel R. de Gruyter; Berlin: 1977

21a Marotta A, Adams CE, Molloy J. Angew. Chem. Int. Ed. 2022; 134: e202207067
21b Pillitteri S, Ranjan P, Van der Eycken EV, Sharma U. Adv. Synth. Catal. 2022; 364: 1643
21c Duret G, Quinlan R, Bisseret P, Blanchard N. Chem. Sci. 2015; 6: 5366

22 Tellis JC, Kelly CB, Primer DN, Jouffroy M, Patel NR, Molander GA. Acc. Chem. Res. 2016; 49: 1429
23 Williams JL. R, Doty JC, Grisdale PJ, Searle R, Regan TH, Happ GP, Maier DP. J. Am. Chem. Soc. 1967; 89: 5153
24 Yasu Y, Koike T, Akita M. Adv. Synth. Catal. 2012; 354: 3414

25a Tellis JC, Primer DN, Molander GA. Science 2014; 345: 433
25b Zuo Z, Ahneman DT, Chu L, Terrett JA, Doyle AG, MacMillan DW. Science 2014; 345: 437
25c Chan AY, Perry IB, Bissonnette NB, Buksh BF, Edwards GA, Frye LI, Garry OL, Lavagnino MN, Li BX, Liang Y, Mao E, Millet A, Oakley JV, Reed NL, Sakai HA, Seath CP, Macmillan DW. C. Chem. Rev. 2022; 122: 1485

26 Hartwig JF. Organotransition Metal Chemistry: From Bonding to Catalysis. University Science; Sausalito: 2010
27 Tasker SZ, Standley EA, Jamison TF. Nature 2014; 509: 299

28a Huang H, Jia K, Chen Y. Angew. Chem. Int. Ed. 2015; 54: 1881
28b Li G.-X, Morales-Rivera CA, Wang Y, Gao F, He G, Liu P, Chen G. Chem. Sci. 2016; 7: 6407
28c Li X, Han M.-Y, Wang B, Wang L, Wang M. Org. Biomol. Chem. 2019; 17: 6612

29 Lima F, Kabeshov MA, Tran DN, Battilocchio C, Sedelmeier J, Sedelmeier G, Schenkel B, Ley SV. Angew. Chem. Int. Ed. 2016; 55: 14085
30 Lima F, Sharma UK, Grunenberg L, Saha D, Johannsen S, Sedelmeier J, Van der Eycken EV, Ley SV. Angew. Chem. Int. Ed. 2017; 56: 15136

For activation with external oxidants, see:

31a Huang H, Zhang G, Gong L, Zhang S, Chen Y. J. Am. Chem. Soc. 2014; 136: 2280
31b Li G.-X, Morales-Rivera CA, Wang Y, Gao F, He G, Liu P, Chen G. Chem. Sci. 2016; 7: 6407
31c Zhang L, Liu Z.-Q. Org. Lett. 2017; 19: 6594
31d Dong J, Yue F, Song H, Liu Y, Wang Q. Chem. Commun. 2020; 56: 12652

For activation with bases, see:

31e Iwata Y, Tanaka Y, Kubosaki S, Morita T, Yoshimi Y. Chem. Commun. 2018; 54: 1257
31f Shi D, Xia C, Liu C. CCS Chem. 2021; 3: 1718

For activation with ArLi, see:

31g Shu C, Noble A, Aggarwal VK. Angew. Chem. Int. Ed. 2019; 58: 3870
31h Clausen F, Kischkewitz M, Bergander K, Studer A. Chem. Sci. 2019; 10: 6210

For solvent-assisted activation approaches, see:

31i Chilamari M, Immel JR, Bloom S. ACS Catal. 2020; 10: 12727
31j Ranjan P, Pillitteri S, Coppola G, Oliva M, Van der Eycken EV, Sharma UK. ACS Catal. 2021; 11: 10862
31k Oliva M, Ranjan P, Pillitteri S, Coppola GA, Messina M, Van der Eycken EV, Sharma UK. iScience 2021; 24: 103134

For dual role of the substrate as Bas activator and reagent, see:

31l Yue F, Dong J, Liu Y, Wang Q. Org. Lett. 2021; 23: 2477
31m Gockel N, Lee S, Gay BL, Hull KL. ACS Catal. 2021; 11: 5166
31n Pillitteri S, Ranjan P, Ojeda-Carralero GM, Vázquez-Amaya LY, Alfonso-Ramos JE, Van der Eycken EV, Sharma UK. Org. Chem. Front. 2022; 9: 6958

32 Speckmeier E, Maier TC. J. Am. Chem. Soc. 2022; 144: 9997
33 Lovering F, Bikker J, Humblet C. J. Med. Chem. 2009; 52: 6752
34 Han F.-S. Chem. Soc. Rev. 2013; 42: 5270
35 DeLano TJ, Bandarage UK, Palaychuk N, Green J, Boyd MJ. J. Org. Chem. 2016; 81: 12525
36 Cauley AN, Sezen-Edmonds M, Simmons EM, Cavallaro CL. React. Chem. Eng. 2021; 6: 1666
37 Lima F, Grunenberg L, Rahman HB, Labes R, Sedelmeier J, Ley SV. Chem. Commun. 2018; 54: 5606

38a de Graaff C, Ruijter E, Orru RV. Chem. Soc. Rev. 2012; 41: 3969
38b Cioc RC, Ruijter E, Orru RV. Green Chem. 2014; 16: 2958
38c Abdelraheem EM, Shaabani S, Dömling A. Drug Discov. Today Technol. 2018; 29: 11

39 Petasis NA, Akritopoulou I. Tetrahedron Lett. 1993; 34: 583
40 Wu P, Givskov M, Nielsen TE. Chem. Rev. 2019; 119: 11245
41 Yi J, Badir SO, Alam R, Molander GA. Org. Lett. 2019; 21: 4853
42 Oliva M, Martens F, Van der Eycken EV, Sharma UK. STAR Protoc. 2022; 3: 101162
43 Vázquez-Amaya L, Dootselaere B, Ojeda-Carralero GM, Pillitteri S, Van der Eycken EV, Sharma UK. ChemRxiv 2023; preprint
44 Minisci F, Bernardi R, Bertini F, Galli R, Perchinummo M. Tetrahedron 1971; 27: 3575
45 Proctor RS, Phipps RJ. Angew. Chem. Int. Ed. 2019; 58: 13666

46a Beatty JW, Douglas JJ, Cole KP, Stephenson CR. J. Nat. Commun. 2015; 6: 7919
46b Mousseau JJ, Perry MA, Bundesmann MW, Chinigo GM, Choi C, Gallego G, Hicklin RW, Hoy S, Limburg DC, Sach NW, Zhang Y. ACS Catal. 2022; 12: 600
46c Graham MA, Noonan G, Cherryman JH, Douglas JJ, Gonzalez M, Jackson LV, Leslie K, Liu Z, McKinney D, Munday RH, Parsons CD, Whittaker DT. E, Zhang E, Zhang J. Org. Process Res. Dev. 2021; 25: 57