Process for generating useful electrophiles from common anions and their application in electrophilic reactions with organic substrates
AssigneeAir Products and Chemicals, Inc.
InventorsRobert George Syvret, Tung Phuong Nguyen, Victoria Lee Bulleck, Ryan Dennis Rieth
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Abstract
A process includes substituting a substituent on a substrate. The process includes reacting a salt of an anionic form of the substituent with an electrophilic fluorination agent to provide an electrophile containing a cationic form of the substituent. The electrophile is then electrophilically substituted on the substrate. In some aspects of the process, the substrate can be an aromatic or a non-aromatic. The process can be used for a variety of reactions having electrophilic mechanisms, including halogenation, thiocyanation and nitration.
Claims21
A process for substituting a substituent on a substrate, said process comprising:
- reacting a salt comprising an anionic form of said substituent with an electrophilic fluorination agent to provide an electrophile comprising a cationic form of said substituent;
- and
- electrophilically substituting said electrophile on said substrate.
A process for electrophilically substituting an electrophile on a substrate, said process being represented by Equation (1):
- wherein F+ is an electrophilic fluorination agent;
- M+ is a cation;
- X− is chloride, bromide, thiocyanate, nitrite, acetate or trifluoroacetate;
- and each of R1-6 is independently a member selected from the group consisting of H, F, Cl, CH3, COOH, C(O)CH3, NO2, OR′ and NR′R″, where R′ and R″ are independently H, C(O)CH3, or CH3.
Dependencies are inferred from the claim text.