scholarly journals Organic synthesis using (diacetoxyiodo)benzene (DIB): Unexpected and novel oxidation of 3-oxo-butanamides to 2,2-dihalo-N-phenylacetamides

2012 ◽  
Vol 8 ◽  
pp. 344-348 ◽  
Author(s):  
Wei-Bing Liu ◽  
Cui Chen ◽  
Qing Zhang ◽  
Zhi-Bo Zhu
Keyword(s):  
Chemical Synthesis ◽  
Organic Synthesis ◽  
Lewis Acid ◽  
Reliable Method ◽  
Hypervalent Iodine ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Direct Preparation

A novel and reliable method for the direct preparation of 2,2-dihalo-N-phenylacetamides is reported. The key transformation involves the cleavage of a carbon–carbon bond in the presence of DIB and a Lewis acid as the halogen source, and thus this method significantly expands the value of DIB as a unique and powerful tool in chemical synthesis. This protocol not only adds a new aspect to reactions that use other hypervalent iodine reagents but also provides a wide space for the synthesis of disubstituted acetamides.

Modern Organic Synthesis in the Laboratory

2008 ◽  
Author(s):  
Jie Jack Li ◽  
Chris Limberakis ◽  
Derek A. Pflum
Keyword(s):  
Organic Chemistry ◽  
Graduate Students ◽  
Organic Synthesis ◽  
Functional Group ◽  
Bond Formation ◽  
Reaction Conditions ◽  
Carbon Bond ◽  
Oxidation Reduction ◽  
Carbon Carbon Bond ◽  
Daunting Task

Searching for reaction in organic synthesis has been made much easier in the current age of computer databases. However, the dilemma now is which procedure one selects among the ocean of choices. Especially for novices in the laboratory, it becomes a daunting task to decide what reaction conditions to experiment with first in order to have the best chance of success. This collection intends to serve as an "older and wiser lab-mate" one could have by compiling many of the most commonly used experimental procedures in organic synthesis. With chapters that cover such topics as functional group manipulations, oxidation, reduction, and carbon-carbon bond formation, Modern Organic Synthesis in the Laboratory will be useful for both graduate students and professors in organic chemistry and medicinal chemists in the pharmaceutical and agrochemical industries.

Hydrolase-catalyzed asymmetric carbon–carbon bond formation in organic synthesis

RSC Advances ◽  
2015 ◽  
Vol 5 (22) ◽  
pp. 16801-16814 ◽  
Author(s):  
Zhi Guan ◽  
Ling-Yu Li ◽  
Yan-Hong He
Keyword(s):  
Organic Synthesis ◽  
Bond Formation ◽  
Carbon Bond ◽  
Bond Forming ◽  
Carbon Carbon Bond ◽  
Bond Forming Reactions ◽  
Asymmetric Carbon

This article reviews the hydrolase-catalyzed asymmetric carbon–carbon bond-forming reactions for the preparation of enantiomerically enriched compounds in organic synthesis.

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