55848-60-7

Upstream product

• 4648-54-8 trimethylsilylazide 
• 20780-53-4 (R)-Styrene oxide 
• 100-42-5 styrene 
• 96-09-3 styrene oxide 

Downstream Products

• 7568-93-6 2-Amino-1-phenylethanol 
• 55848-61-8 2-phenyl-2-(trimethylsiloxy)ethylamine 
• 124718-87-2 2-azido-1-phenylethan-1-ol 

Relevant academic research and scientific papers

A Hafnium-Based Metal-Organic Framework as a Nature-Inspired Tandem Reaction Catalyst

Tandem catalytic systems, often inspired by biological systems, offer many advantages in the formation of highly functionalized small molecules. Herein, a new metal-organic framework (MOF) with porphyrinic struts and Hf6 nodes is reported. This MOF demonstrates catalytic efficacy in the tandem oxidation and functionalization of styrene utilizing molecular oxygen as a terminal oxidant. The product, a protected 1,2-aminoalcohol, is formed selectively and with high efficiency using this recyclable heterogeneous catalyst. Significantly, the unusual regioselective transformation occurs only when an Fe-decorated Hf6 node and the Fe-porphyrin strut work in concert. This report is an example of concurrent orthogonal tandem catalysis.

A waste-minimized protocol for the preparation of 1,2-azido alcohols and 1,2-amino alcohols

Under solvent-free conditions the reaction of epoxides 1a-i with trimethylsilylazide (2) catalyzed by polystiryl-supported fluoride (PS-DABCOF2) has led to the efficient preparation of the corresponding O-TMS protected 1,2-azido alcohols 3a-i that, by treatment with Dowex-H, gave the related 1,2-azido alcohols 4a-i in excellent yields (83-99% and 82-96%, respectively). The use of a flow procedure has allowed us to significantly minimize waste in the preparation of representative 1,2-azido alcohols 4a, 4c and 4i that have been obtained with E-factors of 1.6, 2.1, and 1.9, respectively. The 1,2-amino alcohols 5a, 5c and 5f have been also prepared, in quantitative yields, by reduction of the corresponding O-TMS protected 1,2-azido alcohols 3a, 3c, and 3f by Pd on the Al2O3/HCOOH system.

Modular, active, and robust lewis acid catalysts supported on a metal-organic framework

Metal-organic frameworks (MOFs) have shown promise as heterogeneous catalysts because of their high crystallinity, uniform pores, and ability to be chemically and physically tuned for specific chemical transformations. One of the challenges with MOF-based

MgAlCO3-HT catalyzed ring opening of oxiranes with TMSN3

MgAlCO3-HT is an effective catalyst for the nucleophilic ring opening of oxiranes with TMSN3.

Tetraphenylstibonium Hydroxide-Catalyzed Reaction of Trimethylsilyl Azide with Oxiranes

Tetraphenylstibonium hydroxide was an effective catalyst for the reaction of trimethylsilyl azide with oxiranes to give silylated vicinal azidohydrins.This azidation reaction was chemoselective to the oxirane moieties, while aldehyde was tolerable under t

HIGHLY REGIO AND CHEMOSELECTIVE RING OPENING OF EPOXIDES WITH TRIMETHYLSILYL AZIDE IN THE PRESENCE OF ALUMINIUM ISOPROPOXIDE AND TITANIUM ISOPROPOXIDE

The ring-opening of functionalized epoxides with trimethylsilyl azide in the presence of a catalytic amount of Ti(O-i-Pr)4 or Al(O-i-Pr)3 is described.The reaction is stereospecific and highly regiospecific, leading generally to the formation of the carbon-azido bond on the less substituted carbon.The mechanism of this reaction is also discussed.

OUVERTURE ENANTIODIVERGENTE DE L'EPOXYSTYRENE (R) PAR Me3SiN3 CATALYSEE PAR Al(O-iPr)3 ET Ti(O-iPr)4

Ring-opening of (R) epoxystyrene with Me3SiN3 in the presence of Al(O-iPr)3 gives only the (S) silylated azidohydrine.Use of Ti(O-iPr)4 leads to the enantiodivergent opening of the epoxide, depending upon the solvent used.

Ouverture regioselective d'epoxydes par Me3SiN3 catalysee par Ti(O.iPr)4

Ti(O-iPr)4 catalyzes the ring opening reaction of functionnalised epoxides with Me3SiN3 in a highly regioselective manner.