Applications of Iron Pincer Complexes in Hydrosilylation Reactions

Overview

Journal RSC Adv

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2022 Sep 21

PMID 36128525

Authors

Rasheed Nihala

Kalathingal Nasreen Hisana

C M A Afsina

Gopinathan Anilkumar

Affiliations

Soon will be listed here.

Abstract

Due to its abundance, low cost and low toxicity, the first-row transition metal, iron is widely preferred as a catalyst in organic synthesis. The only drawback of lower selectivity due to high reactivity and low stability of the metal centre is tuned by using pincer ligands of different types. The different iron pincer complexes thus prepared are extensively used in catalyzing different types of organic reactions with great selectivity and functional group tolerance under moderate reaction conditions. In this review, we focus on the applications of iron pincer complexes in hydrosilylation reactions, especially the hydrosilylation of carbonyl derivatives and alkene/alkynes.

References

Chen C, Wang H, Sun Y, Cui J, Xie J, Shi Y . Iron-Catalyzed Asymmetric Hydrosilylation of Vinylcyclopropanes via Stereospecific C-C Bond Cleavage. iScience. 2020; 23(4):100985. PMC: 7115165. DOI: 10.1016/j.isci.2020.100985. View

Zuo Z, Zhang L, Leng X, Huang Z . Iron-catalyzed asymmetric hydrosilylation of ketones. Chem Commun (Camb). 2015; 51(24):5073-6. DOI: 10.1039/c5cc00612k. View

Fleming I, Barbero A, Walter D . Stereochemical Control in Organic Synthesis Using Silicon-Containing Compounds. Chem Rev. 2002; 97(6):2063-2192. DOI: 10.1021/cr941074u. View

Jia X, Huang Z . Conversion of alkanes to linear alkylsilanes using an iridium-iron-catalysed tandem dehydrogenation-isomerization-hydrosilylation. Nat Chem. 2016; 8(2):157-61. DOI: 10.1038/nchem.2417. View

Langlotz B, Wadepohl H, Gade L . Chiral bis(pyridylimino)isoindoles: a highly modular class of pincer ligands for enantioselective catalysis. Angew Chem Int Ed Engl. 2008; 47(25):4670-4. DOI: 10.1002/anie.200801150. View

PIETRUSZA E, SOMMER L, WHITMORE F . A new synthesis of organosilicon compounds. J Am Chem Soc. 1948; 70(2):484-6. DOI: 10.1021/ja01182a014. View

Metsanen T, Gallego D, Szilvasi T, Driess M, Oestreich M . Peripheral mechanism of a carbonyl hydrosilylation catalysed by an SiNSi iron pincer complex. Chem Sci. 2018; 6(12):7143-7149. PMC: 5951209. DOI: 10.1039/c5sc02855h. View

Guo J, Cheng Z, Chen J, Chen X, Lu Z . Iron- and Cobalt-Catalyzed Asymmetric Hydrofunctionalization of Alkenes and Alkynes. Acc Chem Res. 2021; 54(11):2701-2716. DOI: 10.1021/acs.accounts.1c00212. View

Cheng B, Liu W, Lu Z . Iron-Catalyzed Highly Enantioselective Hydrosilylation of Unactivated Terminal Alkenes. J Am Chem Soc. 2018; 140(15):5014-5017. DOI: 10.1021/jacs.8b01638. View

10.

McManus H, Guiry P . Coupling of bulky, electron-deficient partners in aryl amination in the preparation of tridentate bis(oxazoline) ligands for asymmetric catalysis. J Org Chem. 2002; 67(24):8566-73. DOI: 10.1021/jo0262558. View

11.

Zhang P, Li X, Qi X, Sun H, Fuhr O, Fenske D . Transfer hydrogenation of aldehydes catalyzed by silyl hydrido iron complexes bearing a [PSiP] pincer ligand. RSC Adv. 2022; 8(25):14092-14099. PMC: 9079873. DOI: 10.1039/c8ra02606h. View

12.

Wei D, Darcel C . Iron Catalysis in Reduction and Hydrometalation Reactions. Chem Rev. 2018; 119(4):2550-2610. DOI: 10.1021/acs.chemrev.8b00372. View

13.

Chang G, Zhang P, Yang W, Xie S, Sun H, Li X . Pyridine N-oxide promoted hydrosilylation of carbonyl compounds catalyzed by [PSiP]-pincer iron hydrides. Dalton Trans. 2020; 49(27):9349-9354. DOI: 10.1039/d0dt00392a. View

14.

Deng Q, Wadepohl H, Gade L . The synthesis of a new class of chiral pincer ligands and their applications in enantioselective catalytic fluorinations and the Nozaki-Hiyama-Kishi reaction. Chemistry. 2011; 17(52):14922-8. DOI: 10.1002/chem.201102375. View

15.

Denmark S, Regens C . Palladium-catalyzed cross-coupling reactions of organosilanols and their salts: practical alternatives to boron- and tin-based methods. Acc Chem Res. 2008; 41(11):1486-99. PMC: 2648401. DOI: 10.1021/ar800037p. View

16.

Inagaki T, Phong L, Furuta A, Ito J, Nishiyama H . Iron- and cobalt-catalyzed asymmetric hydrosilylation of ketones and enones with bis(oxazolinylphenyl)amine ligands. Chemistry. 2010; 16(10):3090-6. DOI: 10.1002/chem.200903118. View

17.

Lin H, Lutz S, OKane C, Zeller M, Chen C, Al Assil T . Synthesis and characterization of an iron complex bearing a hemilabile NNN-pincer for catalytic hydrosilylation of organic carbonyl compounds. Dalton Trans. 2018; 47(10):3243-3247. DOI: 10.1039/c7dt04928e. View

18.

Chakraborty S, Bhattacharya P, Dai H, Guan H . Nickel and iron pincer complexes as catalysts for the reduction of carbonyl compounds. Acc Chem Res. 2015; 48(7):1995-2003. DOI: 10.1021/acs.accounts.5b00055. View

19.

Biernesser A, Li B, Byers J . Redox-controlled polymerization of lactide catalyzed by bis(imino)pyridine iron bis(alkoxide) complexes. J Am Chem Soc. 2013; 135(44):16553-60. DOI: 10.1021/ja407920d. View

20.

Chen J, Cheng B, Cao M, Lu Z . Iron-catalyzed asymmetric hydrosilylation of 1,1-disubstituted alkenes. Angew Chem Int Ed Engl. 2015; 54(15):4661-4. DOI: 10.1002/anie.201411884. View