19275-61-7

Upstream product

• 493-05-0 isochromane 
• 31253-52-8 α-chloroisochroman 
• 77086-38-5 ketene t-butyldimethylsilyl methyl acetal 

Downstream Products

• 60355-20-6 2'-(2-chloroethyl)benzaldehyde 
• 22901-09-3 2-(2-bromoethyl)benzaldehyde 
• 493-05-0 isochromane 
• 4702-34-5 isochroman-1-one 

Relevant academic research and scientific papers

Catalytic enantioselective oxidative cross-coupling of benzylic ethers with aldehydes

The first one-pot enantioselective oxidative coupling of cyclic benzylic ethers with aldehydes has been developed. A variety of benzylic ethers were transformed into the corresponding oxygen heterocycles with high enantioselectivity. Mechanistic experiments were conducted to determine the nature of the reaction intermediates. The application of this strategy to coupling reactions with other nucleophiles besides aldehydes was also explored. In one go: The first one-pot enantioselective oxidative coupling of cyclic benzylic ethers with aldehydes has been developed. A variety of benzylic ethers could be functionalized with this method, and the corresponding oxygen heterocycles were obtained with high enantioselectivity.

Scalable Aerobic Oxidation of Alcohols Using Catalytic DDQ/HNO3

A selective, practical, and scalable aerobic oxidation of alcohols is described that uses catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and HNO3, with molecular oxygen serving as the terminal oxidant. The method was successfully applied to the oxidation of a wide range of benzylic, propargylic, and allylic alcohols, including two natural products, namely, carveol and podophyllotoxin. The conditions are also applicable to the selective oxidative deprotection of p-methoxybenzyl ethers.

Nitric acid-catalyzed aerobic oxidation of benzylic sp3 C–H bonds of isochromans, xanthenes and 9-fluorenone under additive-free conditions

HNO3 was demonstrated to be an effective catalyst for aerobic oxidation of benzylic sp3 C–H bonds under additive-free conditions. A series of isochromans, xanthenes and fluorenes underwent this transformation to give the targeted products in low to high yields under the catalysis of HNO3, which provided an effective method for the synthesis of the synthetically and biologically valued isochromanones, xanthones and 9-fluorenones.

Catalytic Carbon–Chlorine Bond Activation by Selenium-Based Chalcogen Bond Donors

Chalcogen bonding is a noncovalent interaction based on electrophilic chalcogen substituents, which shares many similarities with the more well-known hydrogen and halogen bonding. Herein, the first application of selenium-based chalcogen bond donors in or

Dehydrogenative α-oxygenation of ethers with an iron catalyst

Selective α-oxidation of ethers under aerobic conditions is a long-pursued transformation; however, a green and efficient catalytic version of this reaction remains challenging. Herein, we report a new family of iron catalysts capable of promoting chemoselective α-oxidation of a range of ethers with excellent mass balance and high turnover numbers under 1 atm of O2 with no need for any additives. Unlike metalloenzymes and related biomimetics, the catalyst produces H2 as the only byproduct. Mechanistic investigations provide evidence for an unexpected two-step reaction pathway, which involves dehydrogenative incorporation of O2 into the ether to give a peroxobisether intermediate followed by cleavage of the peroxy bond to form two ester molecules, releasing stoichiometric H2 gas in each step. The operational simplicity and environmental friendliness of this methodology affords a useful alternative for performing oxidation, while the unique ability of the catalyst in oxygenating a substrate via dehydrogenation points to a new direction for understanding metalloenzymes and designing new biomimetic catalysts.

A New Approach for Oxygenation Using Nitric Oxide under the Influence of N-Hydroxyphthalimide

An approach for partial oxygenation through a carbocation as an intermediate was successfully developed by using nitric oxide under the influence of N-hydroxyphthalimide. Thus, a variety of benzylic ethers were converted into the corresponding partially oxidized compounds, which are difficult to prepare by conventional methods, in high yields. For example, the reaction of phthalane with NO in the presence of a catalytic amount of NHPI at 60°C gave phthalaldehyde in 80% yield. The reaction was found to proceed through the formation of a hemiacetal, such as 1-hydroxyphthalane. In addition, 1,3-di-tert-butoxymethyl benzene afforded 1,3-benzenedicarbaldehyde in good yield. On the other hand, isochroman was converted into 1,1′-oxodiisochromane under these reaction conditions. The reaction of ethers with NO in the presence of a NHPI catalyst is thought to proceed via the formation of a carbocation as an intermediate. A possible reaction path was suggested.