163083-22-5

Upstream product

• 2491-32-9 1-(4-Hydroxyphenyl)-2-phenylethanone 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 123-08-0 4-hydroxy-benzaldehyde 
• 66310-10-9 N-benzyl-2,4,6-triphenylpyridinium tetrafluoroborate 
• 120743-99-9 p-[(tert-butyldimethylsilyl)oxy]benzaldehyde 
• 100-46-9 benzylamine 

Downstream Products

• 191536-17-1 4(t-butyldimethylsilyloxy)-α-phenylphenacyl bromide 
• 919519-15-6 1-hydroxy-1-(4-hydroxyphenyl)-3-methyl-2-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 
• 919519-17-8 1-[4-(t-butyldimethylsilyloxy)phenyl]-1-hydroxy-3-methyl-2-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 
• 919519-07-6 4-t-butyldimethylsilyloxy-N-[2-(2-iodophenyl)ethyl]-N-methyl-α-phenylphenacylamine 
• 942617-87-0 1-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-phenyl-ethanone oxime 

Relevant academic research and scientific papers

C-H Alkylation of Aldehydes by Merging TBADT Hydrogen Atom Transfer with Nickel Catalysis

Catalyst controlled site-selective C-H functionalization is a challenging but powerful tool in organic synthesis. Polarity-matched and sterically controlled hydrogen atom transfer (HAT) provides an excellent opportunity for site-selective functionalization. As such, the dual Ni/photoredox system was successfully employed to generate acyl radicals from aldehydes via selective formyl C-H activation and subsequently cross-coupled to generate ketones, a ubiquitous structural motif present in the vast majority of natural and bioactive molecules. However, only a handful of examples that are constrained to the use of aryl halides are developed. Given the wide availability of amines, we developed a cross-coupling reaction via C-N bond cleavage using the economic nickel and TBADT catalyst for the first time. A range of alkyl and aryl aldehydes were cross-coupled with benzylic and allylic pyridinium salts to afford ketones with a broad spectrum of functional group tolerance. High regioselectivity toward formyl C-H bonds even in the presence of α-methylene carbonyl or α-amino/oxy methylene was obtained.

Iron-Catalyzed Synthesis of Tetrahydronaphthalenes via 3,4-Dihydro-2H-pyran Intermediates

The development of an iron(III)-catalyzed synthetic strategy toward functionalized tetrahydronaphthalenes is described. This approach is characterized by its operational simplicity and is distinct from currently available procedures that rely on [4 + 2]-cycloadditions. Our strategy takes advantage of the divergent reactivity observed for simple aryl ketone precursors to gain exclusive access to tetrahydronaphthalene products (23 examples). Detailed mechanistic investigations identified pyrans as reactive intermediates that afford the desired tetrahydronaphthalenes in high yields upon iron(III)-catalyzed Friedel-Crafts alkylation.

ESTROGEN MODULATORS

The present application is directed to a new class of isoxazoles and their use as estrogen modulators.

Synthesis of new 1,2-Diphenyl-4, 5-dihydro-3H-3-benzazepines

1,2-Diphenyl-4,5-dihydro-3H-3-benzazepine derivatives (2a-d) were synthesized via cyclization reaction of N-[2-(2-iodophenyl)ethyl]-α-phenylphenacylamines (5a-c) and (5e) with n-C4H9Li, followed by dehydration of the cyclization prod