341547-89-5

Upstream product

• 2015-09-0 3-(phenylthio)propylamine 
• 123-11-5 4-methoxy-benzaldehyde 
• 108-98-5 thiophenol 
• 86926-56-9 N-allyl-4-methoxybenzylamine 

Downstream Products

• 341547-96-4 N-(4-methoxyphenyl)methyl-N-[(3-phenylsulfanyl)propyl]formamide 
• 341548-02-5 N-(4-methoxyphenyl)methyl-N-[(3-phenylsulfinyl)propyl]formamide 

Relevant academic research and scientific papers

Rhodium-Catalyzed Regiodivergent Hydrothiolation of Allyl Amines and Imines

The regiodivergent Rh-catalyzed hydrothiolation of allyl amines and imines is presented. Bidentate phosphine ligands with larger natural bite angles (βn ≥ 99°), for example, DPEphos, dpph, or L1, promote a Markovnikov-selective hydrothiolation in up to 88% yield and >20:1 regioselectivity. Conversely, when smaller bite angle ligands (βn ≤ 86°), for example, dppbz or dppp, are employed, the anti-Markovnikov product is formed in up to 74% yield and >20:1 regioselectivity. Initial mechanistic investigations are performed and are consistent with an oxidative addition/olefin insertion/reductive elimination mechanism for each regioisomeric pathway. We hypothesize that the change in regioselectivity is an effect of diverging coordination spheres to favor either Rh-S or Rh-H insertion to form the branched or linear isomer, respectively.

Synthesis of 2,3,4,5-tetrahydro-1H-2-benzazepines via Pummerer-type cyclization of N-arylmethyl-N-(3-phenylsulfinylpropyl) formamides

A construction of 1H-benzazepine ring system was achieved via a modified Pummerer reaction of N-arylmethyl-N-(3-phenylsulfinylpropyl)-formamides (5) using trifluoroacetic acid and borontrifluoride etherate. This method provides an effective synthesis of 7,8-dimethoxy-2,3,4,5-tetrahydro-1H-2-benzazepine (10a), the synthetic intermediate of capsazepine (1), an antagonist of capsaicin and resinferatoxin.