» Articles » PMID: 37981660

Pt(PPh) and Pt(PPh)@IL Catalyzed Hydroboration of Ketones

Overview
Journal Sci Rep
Specialty Science
Date 2023 Nov 20
PMID 37981660
Authors
Affiliations
Soon will be listed here.
Abstract

An efficient method for the reduction of various ketones via [Pt(PPh)]-catalyzed hydroboration with HBpin has been successfully developed for the first time. The protocol is suitable for symmetrical and unsymmetrical derivatives possessing electron donating or withdrawing functional groups. O-borylated products were easily converted to 2° alcohols via hydrolysis with high isolated yields. According to the low-temperature NMR spectroscopy, a reaction mechanism was proposed. Additionally, effective immobilization of the catalyst in the ionic liquid [BMIM][NTf] was applied to increase the productivity of the process by carrying out reactions under the repetitive batch mode, obtaining higher TON values and limiting the amount of expensive Pt used. The catalyst stability and almost neglectable leaching were confirmed by ICP-MS analysis of the extracted mixture. A simple separation method via extraction with n-heptane, efficient catalyst immobilization, and the commercial availability of the Pt complex, make this protocol an attractive method for the hydroboration of ketones.

References
1.
Zhang T, Manna K, Lin W . Metal-Organic Frameworks Stabilize Solution-Inaccessible Cobalt Catalysts for Highly Efficient Broad-Scope Organic Transformations. J Am Chem Soc. 2016; 138(9):3241-9. DOI: 10.1021/jacs.6b00849. View

2.
Stefanowska K, Sokolnicki T, Walkowiak J, Czapik A, Franczyk A . Directed -hydrosilylation of borylalkynes to borylsilylalkenes. Chem Commun (Camb). 2022; 58(86):12046-12049. DOI: 10.1039/d2cc04318a. View

3.
Mahato S, Rawal P, Devadkar A, Joshi M, Roy Choudhury A, Biswas B . Hydroboration and reductive amination of ketones and aldehydes with HBpin by a bench stable Pd(II)-catalyst. Org Biomol Chem. 2022; 20(5):1103-1111. DOI: 10.1039/d1ob02339j. View

4.
Barrios-Vargas L, Abeynayake N, Secrist C, Le N, Edwin Webster C, Donnadieu B . Homogeneous MOF-supported catalysis: a direct comparison of catalytic hydroboration with Ni tripodal PE (E = Si, Ge) complexes. Dalton Trans. 2023; 52(26):8883-8892. DOI: 10.1039/d3dt01328f. View

5.
Kaithal A, Chatterjee B, Gunanathan C . Ruthenium Catalyzed Selective Hydroboration of Carbonyl Compounds. Org Lett. 2015; 17(19):4790-3. DOI: 10.1021/acs.orglett.5b02352. View