Emerging Catalyst Control in Cobalt-Catalyzed Oxidative Hydrofunctionalization Reactions

Rong Zhu

doi:10.1055/s-0039-1690498

Synlett, Table of Contents

Synlett 2019; 30(18): 2015-2021
DOI: 10.1055/s-0039-1690498

synpacts

Emerging Catalyst Control in Cobalt-Catalyzed Oxidative Hydrofunctionalization Reactions

Rong Zhu ∗

Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, P. R. of China Email: rongzhu@pku.edu.cn

› Author Affiliations

Abstract

All articles of this category

Abstract

Oxidative functionalization has emerged as an important pathway in Co-catalyzed hydrogen atom transfer (HAT) hydrofunctionalization reactions. Notably, evidence was found for the participation of organometallic intermediates in such radical-polar crossover processes. These findings provide opportunities for catalyst control that was previously absent in HAT catalysis. In this article, we summarize the recent progress towards this direction involving carbon–heteroatom bond-forming intra- and intermolecular reactions, including work from our own group.

1 Introduction

2 Oxidative Trapping by Solvents and Intramolecular Nucleophiles

3 Intermolecular Oxidative Hydrofunctionalization

4 Conclusion and Outlook

Key words

cobalt - radicals - hydrofunctionalization - iodine - catalysis - hydrogen atom transfer

Full Text

References

References
1 Ruiz-Castillo P, Buchwald SL. Chem. Rev. 2016; 116: 12564
2 Yan M, Lo JC, Edwards JT, Baran PS. J. Am. Chem. Soc. 2016; 138: 12692
3 For an excellent review, see: Crossley SW, Obradors C, Martinez RM, Shenvi RA. Chem. Rev. 2016; 116: 8912

4a Li G, Kuo JL, Han A, Abuyuan JM, Young LC, Norton JR, Palmer JH. J. Am. Chem. Soc. 2016; 138: 7698
4b Li G, Han A, Pulling ME, Estes DP, Norton JR. J. Am. Chem. Soc. 2012; 134: 14662
4c Eisenberg DC, Norton JR. Isr. J. Chem. 1991; 31: 55

5a Isayama S, Mukaiyama T. Chem. Lett. 1989; 18: 1071
5b Kato K, Mukaiyama T. Chem. Lett. 1990; 19: 1395
5c Waser J, Nambu H, Carreira EM. J. Am. Chem. Soc. 2005; 127: 8294
5d Waser J, Carreira EM. J. Am. Chem. Soc. 2004; 126: 5676
5e Gaspar B, Carreira EM. Angew. Chem. Int. Ed. 2007; 46: 4519
5f Gaspar B, Carreira EM. Angew. Chem. Int. Ed. 2008; 47: 5758

6a Hoffmann RW. Chem. Soc. Rev. 2016; 45: 577 ; see also ref. 3

For representative recent examples of related processes:

6b Ma X, Herzon SB. Beilstein J. Org. Chem. 2018; 14: 2259
6c Gui J, Pan CM, Jin Y, Qin T, Lo JC, Lee BJ, Spergel SH, Mertzman ME, Pitts WJ, La Cruz TE, Schmidt MA, Darvatkar N, Natarajan SR, Baran PS. Science 2015; 348: 886
6d Crossley SW, Barabe F, Shenvi RA. J. Am. Chem. Soc. 2014; 136: 16788

7a Demarteau J, Debuigne A, Detrembleur C. Chem. Rev. 2019; 119: 6906
7b Studer A, Curran DP. Angew. Chem. Int. Ed. 2016; 55: 58

For representative examples of metal-complexed radicalophiles:

8a Huang X, Meggers E. Acc. Chem. Res. 2019; 52: 833
8b Chen B, Fang C, Liu P, Ready JM. Angew. Chem. Int. Ed. 2017; 56: 8780

9a Kochi JK. Acc. Chem. Res. 1974; 7: 351
9b Lande SS, Kochi JK. J. Am. Chem. Soc. 1968; 90: 5196

Selected examples:

10a Zhu X, Chiba S. Chem. Soc. Rev. 2016; 45: 4504
10b Peacock DM, Roos CB, Hartwig JF. ACS Cent. Sci. 2016; 2: 647
10c Liang Y, Zhang X, MacMillan DW. C. Nature 2018; 559: 83

Selected examples:

11a Zhu R, Buchwald SL. Angew. Chem. Int. Ed. 2013; 52: 12655
11b Zhu R, Buchwald SL. J. Am. Chem. Soc. 2015; 137: 8069
11c Kainz QM, Matier CD, Bartoszewicz A, Zultanski SL, Peters JC, Fu GC. Science 2016; 351: 681
11d Lin JS, Dong XY, Li TT, Jiang NC, Tan B, Liu XY. J. Am. Chem. Soc. 2016; 138: 9357
11e Wang F, Chen P, Liu G. Acc. Chem. Res. 2018; 51: 2036

12a Shigehisa H, Aoki T, Yamaguchi S, Shimizu N, Hiroya K. J. Am. Chem. Soc. 2013; 135: 10306
12b Shigehisa H, Kikuchi H, Hiroya K. Chem. Pharm. Bull. 2016; 64: 371

13a Shigehisa H, Koseki N, Shimizu N, Fujisawa M, Niitsu M, Hiroya K. J. Am. Chem. Soc. 2014; 136: 13534
13b Shigehisa H, Ano T, Honma H, Ebisawa K, Hiroya K. Org. Lett. 2016; 18: 3622
13c Shigehisa H, Hayashi M, Ohkawa H, Suzuki T, Okayasu H, Mukai M, Yamazaki A, Kawai R, Kikuchi H, Satoh Y, Fukuyama A, Hiroya K. J. Am. Chem. Soc. 2016; 138: 10597
13d Shigehisa H. Chem. Pharm. Bull. 2018; 66: 339

For a related radical hydrofluorination reaction:

13e Shigehisa H, Nishi E, Fujisawa M, Hiroya K. Org. Lett. 2013; 15: 5158

14 Shepard SM, Diaconescu PL. Organometallics 2016; 35: 2446

15a Green SA, Matos JL. M, Yagi A, Shenvi RA. J. Am. Chem. Soc. 2016; 138: 12779
15b Shevick SL, Obradors C, Shenvi RA. J. Am. Chem. Soc. 2018; 140: 12056
15c Matos JL. M, Vasquez-Cespedes S, Gu J, Oguma T, Shenvi RA. J. Am. Chem. Soc. 2018; 140: 16976
15d Green SA, Huffman TR, McCourt RO, van der Puyl V, Shenvi RA. J. Am. Chem. Soc. 2019; 141: 7709

16 Touney EE, Foy NJ, Pronin SV. J. Am. Chem. Soc. 2018; 140: 16982

17a Magnuson RH, Halpern J, Levitin IY, Vol’pin ME. J. Chem. Soc., Chem. Commun. 1978; 44
17b Vol’pin ME, Levitin IY, Sigan AL, Halpern J, Tom GM. Inorg. Chim. Acta 1980; 41: 271
17c Halpern J. Angew. Chem. Int. Ed. 1985; 24: 274

18 Zhou X.-L, Yang F, Sun H.-L, Yin Y.-N, Ye W.-T, Zhu R. J. Am. Chem. Soc. 2019; 141: 7250

Compound 31, 1-hydroxy-1,2-benziodoxol-3(1H)-one (or iodosobenzoic acid, IBA) is a well-known group-transferring oxidant:

19a Brand JP, Fernandez Gonzalez D, Nicolai S, Waser J. Chem. Commun. 2011; 47: 102

For an example of early use:

19b Mahoney WL, Hermodson A. Biochemistry 1979; 18: 381

20 Vol’pin ME, Levitin IY, Sigan AL, Nikitaev AT. J. Organomet. Chem. 1985; 279: 263
21 Quote from ref. 6a.

22a Nielsen LP, Zuend SJ, Ford DD, Jacobsen EN. J. Org. Chem. 2012; 77: 2486
22b Pellissier H, Clavier H. Chem. Rev. 2014; 114: 2775