Iridium-Catalyzed Regioselective Borylation of Substituted Biaryls

Soneela Asghar; Tayyaba Shahzadi; Meshari Alazmi; Xin Gao; Abdul-Hamid Emwas; Rahman S. Z. Saleem; Farhat Batool; Ghayoor A. Chotana

doi:10.1055/s-0036-1591968

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(11): 2211-2220
DOI: 10.1055/s-0036-1591968

paper

Iridium-Catalyzed Regioselective Borylation of Substituted Biaryls

Authors

Soneela Asghar

^aDepartment of Chemistry & Chemical Engineering, Syed Babar Ali School of Science & Engineering, Lahore University of Management Sciences, Lahore 54792, Pakistan eMail: ghayoor.abbas@lums.edu.pk
Tayyaba Shahzadi

^aDepartment of Chemistry & Chemical Engineering, Syed Babar Ali School of Science & Engineering, Lahore University of Management Sciences, Lahore 54792, Pakistan eMail: ghayoor.abbas@lums.edu.pk
Meshari Alazmi

^bKing Abdullah University of Science and Technology (KAUST), Computational Bioscience Research Center (CBRC), Computer, Electrical and Mathematical Sciences and Engineering (CEMSE) Division, Thuwal, 23955-6900, Saudi Arabia
Xin Gao

^bKing Abdullah University of Science and Technology (KAUST), Computational Bioscience Research Center (CBRC), Computer, Electrical and Mathematical Sciences and Engineering (CEMSE) Division, Thuwal, 23955-6900, Saudi Arabia
Abdul-Hamid Emwas

^cKing Abdullah University of Science and Technology (KAUST), Core Labs, Thuwal, 23955-6900, Saudi Arabia
Rahman S. Z. Saleem

^aDepartment of Chemistry & Chemical Engineering, Syed Babar Ali School of Science & Engineering, Lahore University of Management Sciences, Lahore 54792, Pakistan eMail: ghayoor.abbas@lums.edu.pk
Farhat Batool

^aDepartment of Chemistry & Chemical Engineering, Syed Babar Ali School of Science & Engineering, Lahore University of Management Sciences, Lahore 54792, Pakistan eMail: ghayoor.abbas@lums.edu.pk
Ghayoor A. Chotana*

^aDepartment of Chemistry & Chemical Engineering, Syed Babar Ali School of Science & Engineering, Lahore University of Management Sciences, Lahore 54792, Pakistan eMail: ghayoor.abbas@lums.edu.pk

Abstract

Alle Artikel dieser Rubrik

Abstract

Biarylboronic esters are generally prepared by directed ortho-metalation or by Miyaura borylation and hence rely on the presence of a directing group or pre-functionalization. In this paper, the preparation of biarylboronic esters by direct C–H borylation of biaryl substrates is reported. Sterically governed regioselectivities were observed in the borylation of appropriately substituted biaryls by using [Ir(OMe)(COD)]₂ precatalyst and di-tert-butylbipyridyl ligand. The resulting biarylboronic esters were isolated in 38–98% yields. The synthesized biarylboronic esters were further successfully employed in C–O, C–Br, and C–C coupling reactions.

Key words

biaryls - boronic esters - iridium-catalyzed - borylation - regioselective - sterically governed - Suzuki coupling

Volltext

Referenzen

References

1a Ernst JT. Kutzki O. Debnath AK. Jiang S. Lu H. Hamilton AD. Angew. Chem. Int. Ed. 2002; 41: 278
1b Molloy JJ. Law RP. Fyfe JW. B. Seath CP. Hirst DJ. Watson AJ. B. Org. Biomol. Chem. 2015; 13: 3093

2 Li C. Liu M. Pschirer NG. Baumgarten M. Müllen K. Chem. Rev. 2010; 110: 6817
3 Guan A. Liu C. Yang X. Dekeyser M. Chem. Rev. 2014; 114: 7079
4 Manabe K. Ishikawa S. Chem. Commun. 2007; 3829
5 Yang Y. Lan J. You J. Chem. Rev. 2017; 117: 8787

6a Maluenda I. Navarro O. Molecules 2015; 20: 7528
6b Miyaura N. Suzuki A. Chem. Rev. 1995; 95: 2457
6c Suzuki A. J. Organomet. Chem. 1999; 576: 147

7a Yamaguchi J. Yamaguchi AD. Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
7b Okamoto K. Zhang J. Housekeeper JB. Marder SR. Luscombe CK. Macromolecules 2013; 46: 8059
7c Segawa Y. Maekawa T. Itami K. Angew. Chem. Int. Ed. 2015; 54: 66

8 Chauder B. Green L. Snieckus V. Pure Appl. Chem. 1999; 71: 1521
9 Yoshida T. Ilies L. Nakamura E. ACS Catal. 2017; 7: 3199
10 Stappert S. Li C. Müllen K. Basché T. Chem. Mater. 2016; 28: 906
11 Niwa T. Ochiai H. Watanabe Y. Hosoya T. J. Am. Chem. Soc. 2015; 137: 14313
12 Noguchi H. Hojo K. Suginome M. J. Am. Chem. Soc. 2007; 129: 758

13a Fyfe JW. B. Valverde E. Seath CP. Kennedy AR. Redmond JM. Anderson NA. Watson AJ. B. Chem. Eur. J. 2015; 21: 8951
13b Muir CW. Vantourout JC. Isidro-Llobet A. Macdonald SJ. F. Watson AJ. B. Org. Lett. 2015; 17: 6030

14a Cho J.-Y. Tse MK. Holmes D. Maleczka RE. Jr. Smith MR. III. Science 2002; 295: 305
14b Ishiyama T. Takagi J. Ishida K. Miyaura N. Anastasi NR. Hartwig JF. J. Am. Chem. Soc. 2002; 124: 390
14c Ishiyama T. Nobuta Y. Hartwig JF. Miyaura N. Chem. Commun. 2003; 2924
14d Chotana GA. Vanchura II. B. A. Tse MK. Staples RJ. Maleczka RE. Jr. Smith MR. III. Chem. Commun. 2009; 5731
14e Ghaffari B. Vanchura BA. Chotana GA. Staples RJ. Holmes D. Maleczka RE. Jr. Smith MR. III. Organometallics 2015; 34: 4732

15 Dombray T. Werncke CG. Jiang S. Grellier M. Vendier L. Bontemps S. Sortais J.-B. Sabo-Etienne S. Darcel C. J. Am. Chem. Soc. 2015; 137: 4062
16 Furukawa T. Tobisu M. Chatani N. Chem. Commun. 2015; 51: 6508

17a Obligacion JV. Semproni SP. Chirik PJ. J. Am. Chem. Soc. 2014; 136: 4133
17b Obligacion JV. Semproni SP. Pappas I. Chirik PJ. J. Am. Chem. Soc. 2016; 138: 10645
17c Obligacion JV. Bezdek MJ. Chirik PJ. J. Am. Chem. Soc. 2017; 139: 2825
17d Obligacion JV. Chirik PJ. ACS Catal. 2017; 7: 4366
17e Ren H. Zhou Y.-P. Bai Y. Cui C. Driess M. Chem. Eur. J. 2017; 23: 5663

18 Mazzacano TJ. Mankad NP. J. Am. Chem. Soc. 2013; 135: 17258
19 Bheeter CB. Chowdhury AD. Adam R. Jackstell R. Beller M. Org. Biomol. Chem. 2015; 13: 10336

20a Mkhalid IA. I. Barnard JH. Marder TB. Murphy JM. Hartwig JF. Chem. Rev. 2010; 110: 890
20b Hartwig JF. Acc. Chem. Res. 2017; 50: 549
20c Xu L. Wang G. Zhang S. Wang H. Wang L. Liu L. Jiao J. Li P. Tetrahedron 2017; 73: 7123

21 Kallepalli VA. Gore KA. Shi F. Sanchez L. Chotana GA. Miller SL. Maleczka RE. Jr. Smith MR. III. J. Org. Chem. 2015; 80: 8341

22a Finke AD. Moore JS. Org. Lett. 2008; 10: 4851
22b Eliseeva MN. Scott LT. J. Am. Chem. Soc. 2012; 134: 15169
22c Yamaguchi R. Ito S. Lee BS. Hiroto S. Kim D. Shinokubo H. Chem. Asian J. 2013; 8: 178
22d Ikemoto K. Yoshii A. Izumi T. Taka H. Kita H. Xue JY. Kobayashi R. Sato S. Isobe H. J. Org. Chem. 2016; 81: 662
22e Zhang G. Rominger F. Mastalerz M. Chem. Eur. J. 2016; 22: 3084

23a Chang Y. Lee HH. Kim SH. Jo TS. Bae C. Macromolecules 2013; 46: 1754
23b Mohanty AD. Lee Y.-B. Zhu L. Hickner MA. Bae C. Macromolecules 2014; 47: 1973
23c Chang Y. Mohanty AD. Smedley SB. Abu-Hakmeh K. Lee YH. Morgan JE. Hickner MA. Jang SS. Ryu CY. Bae C. Macromolecules 2015; 48: 7117

24 Crawford KM. Ramseyer TR. Daley CJ. A. Clark TB. Angew. Chem. Int. Ed. 2014; 53: 7589
25 Kalläne SI. Braun T. Angew. Chem. Int. Ed. 2014; 53: 9311

26a Paul S. Chotana GA. Holmes D. Reichle RC. Maleczka RE. Jr. Smith MR. III. J. Am. Chem. Soc. 2006; 128: 15552
26b Kawamorita S. Miyazaki T. Ohmiya H. Iwai T. Sawamura M. J. Am. Chem. Soc. 2011; 133: 19310
26c Ros A. Estepa B. López-Rodríguez R. Álvarez E. Fernández R. Lassaletta JM. Angew. Chem. Int. Ed. 2011; 50: 11724

27 Ahmed I. Clark DA. Org. Lett. 2014; 16: 4332

28a Robbins DW. Hartwig JF. Org. Lett. 2012; 14: 4266
28b Jayasundara CR. K. Unold JM. Oppenheimer J. Smith MR. III. Maleczka RE. Jr. Org. Lett. 2014; 16: 6072

29 Batool F. Parveen S. Emwas A.-H. Sioud S. Gao X. Munawar MA. Chotana GA. Org. Lett. 2015; 17: 4256
30 Chotana GA. Rak MA. Smith MR. III. J. Am. Chem. Soc. 2005; 127: 10539

Zusatzmaterial

Supporting Information (PDF)