Recent Advances in Heterogeneous Ir Complex Catalysts for Aromatic C–H Borylation

Kyogo Maeda; Ken Motokura

doi:10.1055/a-1478-6118

Synthesis, Table of Contents

Synthesis 2021; 53(18): 3227-3234
DOI: 10.1055/a-1478-6118

special topic

Bond Activation – in Honor of Prof. Shinji Murai

Recent Advances in Heterogeneous Ir Complex Catalysts for Aromatic C–H Borylation

Kyogo Maeda

^aDepartment of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama, 226-8502, Japan

,

Ken Motokura ∗

^aDepartment of Chemical Science and Engineering, School of Materials and Chemical Technology, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama, 226-8502, Japan

^bDepartment of Chemistry and Biotechnology, Yokohama National University, 79-5 Tokiwadai, Hodogaya-ku, Yokohama 240-8501, Japan

› Author Affiliations

Abstract

All articles of this category

Abstract

Aromatic C–H borylation catalyzed by an Ir complex is among the most powerful methods for activating inert bonds. The products, i.e., arylboronic acids and their esters, are usable chemicals for the Suzuki–Miyaura cross-coupling reaction, and significant effort has been directed toward the development of homogeneous catalysis chemistry. In this short review, we present a recent overview of current heterogeneous Ir-complex catalyst developments for aromatic C–H borylation. Not only have Ir complexes been immobilized on support surfaces with phosphine and bipyridine ligands, but Ir complexes incorporated within solid materials have also been developed as highly active and reusable heterogeneous Ir catalysts. Their catalytic activities and stabilities strongly depend on their surface structures, including linker length and ligand structure.

1 Introduction and Homogeneous Ir Catalysis

2 Heterogeneous Ir Complex Catalysts for C–H Borylation Reactions

3 Other Heterogeneous Metal Complex Catalysts for C–H Borylation Reactions

4 Summary and Outlook

Keywords

C–H borylation - Ir complex - heterogeneous catalyst - supported catalyst - bipyridine ligand

Full Text

References

References
1 Xu L, Wang G, Zhang S, Wang H, Wang L, Liu L, Jiao J, Li P. Tetrahedron 2017; 73: 7123

2a Hartwig JF. Acc. Chem. Res. 2012; 45: 864
2b Hartwig JF. Chem. Soc. Rev. 2011; 40: 1992

3 Yamaguchi J, Yamaguchi AD, Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
4 Kotha S, Lahiri K, Kashinath D. Tetrahedron 2002; 58: 9633

5a Iverson CN, Smith MR. III. J. Am. Chem. Soc. 1999; 121: 7696
5b Cho J.-Y, Tse MK, Holmes D, Maleczka RE. Jr, Smith MR. III. Science 2002; 295: 305

6a Press LP, Kosanovich AJ, McCulloch BJ, Ozerov OV. J. Am. Chem. Soc. 2016; 138: 9487
6b Bheeter CB, Chowdhury AD, Adam R, Jackstell R, Beller M. Org. Biomol. Chem. 2015; 13: 10336
6c Davis HJ, Mihai MT, Phipps RJ. J. Am. Chem. Soc. 2016; 138: 12759
6d Yan G, Jian Y, Kuang C, Wang S, Liu H, Zhang Y, Wang J. Chem. Commun. 2010; 46: 3170

7 Ishiyama T, Takagi J, Ishida K, Miyaura N, Natia RA, Hartwig JF. J. Am. Chem. Soc. 2002; 124: 390
8 Boller TM, Murphy JM, Hapke M, Ishiyama T, Miyaura N, Hartwig JF. J. Am. Chem. Soc. 2005; 127: 14263
9 Ishiyama T, Takagi J, Hartwig JF, Miyaura N. Angew. Chem. Int. Ed. 2002; 41: 3056
10 Oeschger RJ, Larsen MA, Bismuto A, Hartwig JF. J. Am. Chem. Soc. 2019; 141: 16479
11 Larsen MA, Hartwig JF. J. Am. Chem. Soc. 2014; 136: 4287
12 Kawamorita S, Ohmiya H, Hara K, Fukuoka A, Sawamura M. J. Am. Chem. Soc. 2009; 131: 5058

13a Tagata T, Nishida M. Tetrahedron Lett. 2009; 50: 6176
13b Tagata T, Nishida M, Nishida A. Adv. Synth. Catal. 2010; 352: 1662
13c Nishida M, Tagata T. J. Synth. Org. Chem. Jpn. 2011; 69: 1212

14 Wu F, Feng Y, Jones VW. ACS Catal. 2014; 4: 1365
15 Maegawa Y, Inagaki S. Dalton Trans. 2015; 44: 13007
16 Waki M, Maegawa Y, Hara K, Goto Y, Shirai S, Yamada Y, Mizoshita N, Tani T, Chun W.-J, Muratsugu S, Toda M, Fukuoka A, Inagaki S. J. Am. Chem. Soc. 2014; 136: 4003
17 Sawano T, Lin Z, Boures D, An B, Wang C, Lin W. J. Am. Chem. Soc. 2016; 138: 9783
18 Manna K, Zhang T, Lin W. J. Am. Chem. Soc. 2014; 136: 6566
19 Gonzalez MI, Bloch ED, Mason JA, Teat SJ, Long JR. Inorg. Chem. 2015; 54: 2995
20 Manna K, Zhang T, Greene FX, Lin W. J. Am. Chem. Soc. 2015; 137: 2665
21 Tahir N, Miranda FM, Everaeit J, Tack P, Heugebaert T, Leus K, Vincze L, Stevens CV, Speybroeck V, Van der Voort P. J. Catal. 2019; 371: 135
22 Vardhan H, Pan Y, Yang Z, Verma G, Nafady A, Al-Enizi AM, Alotaibi TM, Almaghrabi OA, Ma S. APL Mater. 2019; 7: 101111
23 Maeda K, Uemura Y, Chun W.-J, Satter SS, Nakajima K, Manaka Y, Motokura K. ACS Catal. 2020; 10: 14552
24 Zhuang Z, Wang Y, Chen Z, Wang D, Chen C, Peng Q, Li Y. Mater. Chem. Front. 2020; 4: 1158
25 Newer R, Begum W, Antil N, Shukla S, Kumar A, Akhtar N, Balendra S, Manna K. Inorg. Chem. 2020; 59: 10473
26 Dhakshinamoorthy A, García CV, Concepcion P, Garcia H. Catal. Today 2021; 366: 212