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A General Catalytic Method for Highly Cost- and Atom-Efficient Nucleophilic Substitutions.
Peter H Huy1, Isabel Filbrich1
1Institute of Organic Chemistry, Saarland University, P. O. Box 151150, 66041, Saarbruecken, Germany.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|March 7, 2018
Summary
A new formamide-catalyzed method efficiently converts alcohols to alkyl chlorides using trichlorotriazine (TCT). This cost-effective and scalable process offers high atom economy and functional group compatibility, with applications in drug synthesis.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Efficient synthesis of alkyl chlorides from alcohols is crucial in organic chemistry.
- Existing methods often suffer from poor atom economy, harsh conditions, or limited substrate scope.
Purpose of the Study:
- To develop a general, efficient, and scalable protocol for converting alcohols and carboxylic acids into alkyl chlorides.
- To explore the use of trichlorotriazine (TCT) as a chlorinating agent with enhanced atom economy.
Main Methods:
- A formamide-catalyzed reaction utilizing substoichiometric amounts of trichlorotriazine (TCT).
- Investigation of TCT-mediated dihydroxychlorination, transferring all three chlorine atoms.
Main Results:
- Achieved efficient transformation of alcohols to alkyl chlorides with high functional-group compatibility and stereoselectivity.
- Demonstrated excellent atom economy (E-factors down to 4) and scalability (>50 g).
- Developed a one-pot protocol for synthesizing amines, azides, ethers, and sulfides, including the drug rivastigmine.
Conclusions:
- The presented method offers a cost-effective, environmentally friendly, and versatile approach for alkyl chloride synthesis.
- The high atom economy and byproduct profile (cyanuric acid) enhance the sustainability of the process.
- The method's practical utility is validated by the successful synthesis of rivastigmine with stereochemical control.
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