1416982-13-2

Upstream product

• 58774-83-7 [(2-methoxyphenyl)methyl]dimethylamine 
• 333-27-7 methyl trifluoromethanesulfonate 
• 6850-57-3 2-methoxybenzylamine 
• 50-00-0 formaldehyd 
• 124-40-3 dimethyl amine 

Downstream Products

• 30567-87-4 2,4'-dimethoxydiphenylmethane 
• 1310048-96-4 2-(2-methoxybenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1225483-64-6 1-(2-methoxy-benzyl)-1H-indole 
• 159386-46-6 (2-methoxybenzyl)diphenylphosphine oxide 
• 42778-12-1 1-methoxy-2-<(phenylseleno)methyl>benzene 
• 124915-16-8 C₁₆H₁₈O₂Se₂ 

Relevant academic research and scientific papers

Synthesis of Dibenzylic Diselenides from Elemental Selenium and Benzylic Quaternary Ammonium Salts

Abstract: Substituted dibenzyl diselenides are synthesized in good yields (74–91 %) by SN2 nucleophilic substitution of benzylic trimethylammonium salts and diselenide dianion (Se2?), in situ generated from elemental selenium, under

Transition metal-free coupling reactions of benzylic trimethylammonium salts with di(hetero)aryl disulfides and diselenides

A new protocol was developed to synthesize (enantioenriched) thioethers and selenoethers from (chiral) benzylic trimethylammonium salts and di(hetero)aryl disulfides or diselenides. These syntheses were promoted by the presence of weak base and did not require the use of any transition metal, and resulted in the target products with good to excellent yields (72-94%). Using quaternary ammonium salts synthesized from enantiomerically enriched amines led to highly enantiopure benzylic thioethers and selenoethers (94-99% ee) with configurations reversed from those of their enantioenriched quaternary ammonium salts. This journal is

Palladium-Catalyzed C-N Cross-Coupling of NH-Heteroarenes and Quaternary Ammonium Salts via C-N Bond Cleavage

In this paper, we extend the substrate class of Buchwald-Hartwig amination to quaternary ammonium salts. In the presence of Pd(OAc)2 and t-BuXPhos, the coupling of aryl- or arylmethyltrimethylammonium triflates with NH-heteroarenes via C-N bond cleavage affords the desired N-aryl or N-arylmethyl heteroarenes in moderate to excellent yields.

Reductive Coupling between C-N and C-O Electrophiles

The cross-electrophile reaction is a promising strategy for C-C bond formation. Recent studies have focused mainly on reactions with organic halides. Here we report a coupling reaction between C-N and C-O electrophiles that demonstrates the possibility of constructing a C-C bond via C-N and C-O cleavage. Several reactions between benzyl/aryl ammonium salts and vinyl/aryl C-O electrophiles have been studied. Preliminary mechanistic studies revealed that the benzyl ammoniums were activated through a radical mechanism.

Nickel-Catalyzed Borylation of Aryl- and Benzyltrimethylammonium Salts via C-N Bond Cleavage

By developing a mild Ni-catalyzed system, a method for direct borylation of sp2 and sp3 C-N bonds has been established. The key to this hightly efficient C-N bond borylative cleavage depends on the appropriate choice of the nickel catalyst Ni(COD)2, ICy·HCl as a ligand, and the use of 2-ethoxyethanol as the cosolvent. This transformation shows good functional group compatibility and can serve as a powerful synthetic tool for gram-scale synthesis and late-stage C-N borylation of complex compounds.

Nickel-catalyzed cross couplings of benzylic ammonium salts and boronic acids: Stereospecific formation of diarylethanes via C-N bond activation

We have developed a nickel-catalyzed cross coupling of benzylic ammonium triflates with aryl boronic acids to afford diarylmethanes and diarylethanes. This reaction proceeds under mild reaction conditions and with exceptional functional group tolerance. Further, it transforms branched benzylic ammonium salts to diarylethanes with excellent chirality transfer, offering a new strategy for the synthesis of highly enantioenriched diarylethanes from readily available chiral benzylic amines.