21463-98-9

Upstream product

• 127047-12-5 5-phenyl-hex-5-en-1-ol 
• 98-80-6 phenylboronic acid 
• 928-90-5 5-hexyl-1-ol 
• 4203-44-5 2-phenyltetrahydropyran 
• 74-88-4 methyl iodide 
• 1059695-87-2 3-benzoyl-3,4,5,6-tetrahydro-2H-pyran-2-one 
• 98-88-4 benzoyl chloride 

Downstream Products

• 28591-17-5 5-phenylhexan-1-ol 

Relevant academic research and scientific papers

Indium Catalyzed Hydrofunctionalization of Styrene Derivatives Bearing a Hydroxy Group with Organosilicon Nucleophiles

Hydrofunctionalization is one of the most important transformation reactions of alkenes. Herein, we describe the development of an indium-triiodide-catalyzed hydrofunctionalization of alkenes bearing a hydroxy group using various types of organosilicon nucleophiles. Indium triiodide was the most effective catalyst, whereas typical Lewis acids such as TiCl4, AlCl3, and BF3·OEt2 were ineffective. Many functional groups were successfully introduced, and these resulted in yields of 31-86%. Various styrene derivatives were also applicable to this reaction. Mechanistic investigation revealed that the present hydrofunctionalization proceeded through Br?nsted acid-catalyzed intramolecular hydroalkoxylation of alkenes followed by InI3-catalyzed substitution reaction of cyclic ether intermediates.

Toward Customized Tetrahydropyran Derivatives through Regioselective α-Lithiation and Functionalization of 2-Phenyltetrahydropyran

In this contribution, the first direct and efficient functionalization of the preformed 2-phenyltetrahydropyran (2-PhTHP) nucleus by electrophilic interception of the corresponding α-lithiated derivative by employing sBuLi as the base and THF as the solvent at –78 °C was explored. The presence of N,N,N′,N′-tetramethylethylenediamine (TMEDA) proved to be critical to governing reaction feasibility both in polar and apolar solvents and for improving the yield of the reaction. Both carbon- and heteroatom-based halides were found to be competent electrophiles for this transformation, as well as aliphatic and aromatic aldehydes and ketones, isocyanates, and carboxylic acid derivatives. The combination of hexane/TMEDA lowered the rate of racemization of α-lithiated optically active 2-PhTHP, which thereby enabled calculation of its barrier to inversion at –78 °C.

Reagents for diverse iodosilane-mediated transformations

It was observed that a PhSiH2I-mediated protocol using PhSiH3 and cat. I2 caused the deiodination of 2-(iodomethyl)-2-phenyltetrahydrofuran. Stemming from the investigation of the mechanism, we found that the PhSiH3/

Intramolecular Hydroalkoxylation of Unactivated Alkenes Using Silane-Iodine Catalytic System

A novel catalytic system using I2 and PhSiH3 for the intramolecular hydroalkoxylation of unactivated alkenes is described. NMR study indicated that in situ generated PhSiH2I is a possible active catalytic species. This catalytic system allows an efficient intramolecular hydroalkoxylation of phenyl-, trialkyl-, and 1,1-dialkyl-substituted alkenes as well as a variety of unactivated monoalkyl- and 1,2-dialkyl-substituted alkenes at room temperature. Mechanistic consideration based on significant experimental observations is also discussed.

α-Methoxy-benzylmetals: Original synthesis and reactivity

Although 1-methoxy-1-methylseleno-toluene is efficiently metallated by KDA, the same compound as well as its higher homologues react with t-butyllithium producing 1-methoxy benzyllithiums via the C-Se bond cleavage. These species are efficiently alkylated by alkyl halides, even the secondary ones and react with THF in the presence of BF3-OEt2 to produce the homologated tetrahydropyran derivative in good yield.