54872-17-2

Upstream product

• 106-24-1 Geraniol 
• 93-97-0 benzoic acid anhydride 
• 98-88-4 benzoyl chloride 
• 85909-02-0 N-benzyl-N-(tert-butoxycarbonyl)-benzamide 
• 624-15-7 geraniol 
• 5145-65-3 N-benzoylpyrrole 
• 65-85-0 benzoic acid 
• 109598-71-2 1-benzoyloxy-3,7-dimethyl-oct-6-en-3-ol 

Downstream Products

• 94444-18-5 3,7-dimethyl-n-octan-1-yl benzoate 
• 1194244-49-9 (S)-(3,7-dimethyloct-6-enyl)benzene 

Relevant academic research and scientific papers

Ni-catalyzed direct alcoholysis of N-acylpyrrole-type tertiary amides under mild conditions

N-Acylpyrrole-type amides are a class of versatile building blocks in asymmetric synthesis. We report that by employing Ni(COD)2/2,2′-bipyridine (5 mol%) catalytic system, the direct, catalytic alcoholysis of N-acylpyrrole-type aromatic and aliphatic amides with both primary and secondary alcohols can be achieved efficiently under very mild conditions (rt, 1 h) even at gram scale. By increasing the catalyst loading to 10 mol%, prolonging reaction time (18 h), and/or elevating reaction temperature to 50 °C/80 °C, the reaction could be extended to both complex and hindered N-acylpyrroles as well as to N-acylpyrazoles, Nacylindoles, and to other (functionalized) primary and secondary alcohols. In all cases, only 1.5 equiv. of alcohol were used. The value of the method has been demonstrated by the racemization-free, catalytic alcoholysis of chiral amides yielded from other asymmetric methodologies.

Formamide catalyzed activation of carboxylic acids-versatile and cost-efficient amidation and esterification

A novel, broadly applicable method for amide C-N and ester C-O bond formation is presented based on formylpyrrolidine (FPyr) as a Lewis base catalyst. Herein, trichlorotriazine (TCT), which is the most cost-efficient reagent for OH-group activation, was employed in amounts of ≤40 mol% with respect to the starting material (100 mol%). The new approach is distinguished by excellent cost-efficiency, waste-balance (E-factor down to 3) and scalability (up to >80 g). Moreover, high levels of functional group compatibility, which includes acid-labile acetals and silyl ethers, are demonstrated and even peptide C-N bonds can be formed. In comparison to reported amidation procedures using TCT, yields are considerably improved (for instance from 26 to 91%) and esterification is facilitated for the first time in synthetically useful yields. These significant enhancements are rationalized by activation by means of acid chlorides instead of less electrophilic acid anhydride intermediates.

Preparation method for synthesizing ester compound by using N-Boc amide as raw material

The invention relates to a preparation method for synthesizing an ester compound by using N-Boc amide as a raw material. According to the method, an inorganic base is used as a catalyst; the N-Boc amide is subjected to an intermolecular nucleophilic substitution reaction with various alcohol compounds; and various ester compounds can be efficiently obtained. The method has the advantages of beingmild in reaction condition, simple and convenient to operate, high in yield and favorable in functional-group compatibility.

Highly Active Manganese-Mediated Acylation of Alcohols with Acid Chlorides or Anhydrides

To explore further the practical uses of highly active manganese (Mn?), a variety of alcohols were treated with Mn?, and the resulting complexes were coupled with acid chlorides and/or acetic anhydride in the absence of any extra catalyst. The subsequent reactions took place smoothly under mild conditions, providing the corresponding O-acylation products in good to excellent isolated yields.