Recent Advances in C-B Bond Formation through a Free Radical Pathway
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1 Recent Advances in C-B Bond Formation through a Free Radical Pathway G. Yan. D. Huang, X. Wu, Adv. Synth. Catal. 2017, 359, 188. Daniel Meyer University of Bern , Topic Review
2 Classical Methodes 2
3 Classical Methodes Addition of R MgX or R Li E. Khotinsky and M. Melamed, Ber. Dtsch. Chem. Ges. 1909, 42, Miyaura Borylation T. Ishiyama, M. Murata, N. Miyaura, J. Org. Chem. 1995, 60,
4 Classical Methodes Miyaura Borylation 4
5 Classical Methodes Selective Borylation of C-H bonds (Rh or Ir catalysis) I. A. I. Mkhalid, J. H. Bernard, T. B. Marder, J. M. Murphy, J. F. Hartwig, Chem. Rev. 2010, 100,
6 Classical Methodes 6
7 C-B formation through free radical pathways Arylamine derivatives Alkynes Carboxylic acid derivatives (Pseudo)halides 7
8 Borylation of Arylamine Derivatives 8
9 Reactivity Diazonium Salts > Aryldiazonium salts are excellent source of aryl radicals > Often used as oxidative quenchers in photoredox chemistry M. R. Heinrich, Chem. Eur. J. 2009, 15,
10 Borylation Diazonium Salts M. R. Heinrich, Chem. Eur. J. 2009, 15,
11 Borylation of Arylamines via Diazonium Salts Reaction significantly affected by steric and electronic effects > Not working with heteroaromarics > Addition of TEMPO dramatically decrease the yield F. Y. Mo, Y. B. Jiang, D. Qui, Y. Zhang, J. Wang, Angew. Chem. Int. Ed. 2010, 49,
12 Borylation of Arylamines via Diazonium Salts F. Y. Mo, Y. B. Jiang, D. Qui, Y. Zhang, J. Wang, Angew. Chem. Int. Ed. 2010, 49,
13 Borylation of Arylamines via Diazonium Salts D. Qiu, Y. Zhang, J. Wang, Org. Chem. Front. 2014, 1,
14 Borylation of Diazonium Salts using Eosin Y - Reaction significantly affected by steric and electronic effects - Not working with heteroaromarics J. Yu, L. Zhang, F. Yan, Adv. Synth. Catal. 2012, 354,
15 Borylation of Arylamine via Diazonium Salts using Eosin Y In situ diazotization with tbuono S. Ahammed, S. Nandi, D. Kundu, B. C. Ranu, Tetrahedron Lett. 2016, 57,
16 Borylation of Arylamines via Diazonium Salts Addition of 1 equiv TEMPO decrease the yield from 62% to 6% No Phenol-derivatives found W. Erb, A. Hellal, M. Albini, J. Rouden, J. Blanchet, Chem. Eur. J. 2014, 20,
17 Borylation of Diazonium Salts using Zn Electron donating- and withdrawinggroups and halogens (F, Cl, Br, I) X. Qi, L.-B. Jiang, C. Zhou, J.-B. Peng, X.-F. Wu, ChemistryOpen. 2017, 6,
18 Borylation of Aryltriazenes Electron donating-group and halogens (F, Cl, Br, I) S N Ar C. Zhu, M. Yamane, Org. Lett. 2012, 14,
19 Borylation of Benzotriazoles Additive-based robustness screen was performed: Alkene, alkyne, nitril, ester, indol, etc. Alkylation and thiolation was also successfully achieved M. Teders, A. Gómez-Suárez, L. Pitzer, M. N. Hopkinson, F. Glorius, Angew. Chem. Int. Ed. 2017, 56,
20 Borylation of Benzotriazoles M. Teders, A. Gómez-Suárez, L. Pitzer, M. N. Hopkinson, F. Glorius, Angew. Chem. Int. Ed. 2017, 56,
21 Borylation of Aryl (Pseudo)halides 21
22 Borylation of Arylhalides under UV High functional group tolerance (EWG, EDG and pyridine-derivatives) ortho-, meta- or para-substitution gave good yields Addition of Bu 3 SnH = more reduced product Addition TEMPO = lower yield Reaction needs quartz test tube and 300 W high pressure mercury lamp. K. Chen. S. Zhang, P. He, P. Li, Chem Sci. 2016, 7,
23 Borylation of Arylhalides under UV Batch reaction K. Chen. S. Zhang, P. He, P. Li, Chem Sci. 2016, 7,
24 Borylation of Arylhalides under UV Continuous-flow reaction K. Chen. S. Zhang, P. He, P. Li, Chem Sci. 2016, 7,
25 Borylation of Arylhalides under UV K. Chen. S. Zhang, P. He, P. Li, Chem Sci. 2016, 7,
26 Borylation of Aryl(pseudo)halides under UV Needs a EDG-group Tolerates free OH- and NH 2 groups Reaction needs 300 W high pressure mercury lamp. K. Chen. M. S. Cheung, Z. Lin, P. Li, Org. Chem. Front. 2016, 3,
27 Borylation of Aryl(pseudo)halides under UV DFT study MECP = minimum energy crossing point K. Chen. M. S. Cheung, Z. Lin, P. Li, Org. Chem. Front. 2016, 3,
28 Borylation of Aryl(pseudo)halides under UV Needs a EDG-group for F and Cl Boronic esters were also prepared A. M. Mfuh, J. D. Doyle, B. Chhetri, H. D. Arman, O. V. Larionov, J. Am. Chem. Soc. 2016, 138,
29 Diborylation of Arylhalides under UV in IPA = 1,2 diborylation in HFIP = 1,3 diborylation Substituents can change the selectivity O. V. Larionov et al., J. Am. Chem. Soc. 2016, 138,
30 Diborylation of Arylhalides under UV O. V. Larionov et al., J. Am. Chem. Soc. 2016, 138,
31 Borylation Arylhalides under VIS EWG and EDG worked well Primary and secondary alkylbromides worked as well ESR showed that a C- centred (sextet) and N- centred radical are formed (quartet) Normal conditions No Ir-catalyst No substrate No nbu 3 N M. Jiang, H. Yang, H. Fu, Org. Lett. 2016, 18,
32 Borylation Arylhalides under VIS M. Jiang, H. Yang, H. Fu, Org. Lett. 2016, 18,
33 Borylation of Arylhalides EWG and EDG worked well 5-exocyclizations and HAT from THF to prove that radical involved L. Zhang, L. Jiao, J. Am. Chem. Soc. 2017, 139,
34 Borylation of Arylhalides L. Zhang, L. Jiao, J. Am. Chem. Soc. 2017, 139,
35 Borylation of Arylhalides EWG and EDG worked well S. Pinet, V. Liautard, M. Debiais, M. Pucheault, Synthesis 2017, 49,
36 Borylation of Phenol Derivatives EWG and EDG worked well Without NaI only 5% yield First arylborylation from phenol derivatives without transition metals K. Chen. M. S. Cheung, Z. Lin, P. Li, Org. Chem. Front. 2016, 3, 875. W. Liu, X. Yang, Y. Gao, C.-J. Li, J. Am. Chem. Soc. 2017, 139,
37 Borylation of Phenol Derivatives W. Liu, X. Yang, Y. Gao, C.-J. Li, J. Am. Chem. Soc. 2017, 139,
38 Borylation of Carboxylic Acid Derivatives 38
39 Borylation of Aryl-N-Hydroxyphthalimide esters EWG, EDG and halogen L. Candish, M. Teders, F. Glorius, J. Am. Chem. Soc. 2017, 139,
40 Borylation of Alkyl-N-Hydroxyphthalimide esters D. Hu L. Wang, P. Li, Org. Lett. 2017, 19,
41 Borylation of Alkyl-N-Hydroxyphthalimide esters D. Hu L. Wang, P. Li, Org. Lett. 2017, 19,
42 Borylation of Alkyl-N-Hydroxyphthalimide esters D. Hu L. Wang, P. Li, Org. Lett. 2017, 19,
43 Borylation of Alkyl-N-Hydroxyphthalimide esters A. Fawcett, J. Pradeilles, Y. Wang, T. Mutsuga, E. L. Myers, V. K. Aggarwal, Siences. 2017, 357,
44 Borylation of Alkyl-N-Hydroxyphthalimide esters A. Fawcett, J. Pradeilles, Y. Wang, T. Mutsuga, E. L. Myers, V. K. Aggarwal, Siences. 2017, 357,
45 Borylation of Alkynes 45
46 Borylation of Alkynes CO 2 Me, Cl, CN CO 2 Me, Cl, CN, OH, OMe A. Ogawa et al., Chem. Eur. J. 2015, 21, A. Ogawa et al., Tetrahedron 2016, 72,
47 Borylation of Alkynes A. Ogawa et al., Tetrahedron 2016, 72,
48 Thank you for your attention 48
49 Borylation of arylamine derivatives higer catalyst lodading determinal for reaction L. D. Marciasini, N. Richy, M. Vaultier, M. Pucheault, Adv. Synth. Catal. 2013, 355,
50 Borylation of arylamine derivatives L. D. Marciasini, N. Richy, M. Vaultier, M. Pucheault, Adv. Synth. Catal. 2013, 355,
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