Ultrafast flow synthesis of functionalized sulfonyl fluorides and subsequent sufex connections via lithiated chemistry

An ultra-fast synthesis apparatus of an ortho-functionalized benzenesulfonyl fluoride derivative, the apparatus comprising:

• a first micromixer M1 which prepares a first mixture by mixing a benzenesulfonyl fluoride derivative represented by Formula 1 and an organolithium represented by structural formula 2 in reaction scheme 1;
• a first microreactor R1 which receives the first mixture from the first micromixer M1 and reacts it to synthesize an intermediate represented by structural formula 3;
• a second micromixer M2 which prepare a second mixture by mixing the intermediate supplied from the first microreactor R1 and an electrophile;
• and
• a second microreactor R2 which receives the second mixture from the second micromixer M2 and reacts it to synthesize a compound represented by structural formula 4 or a compound represented by structural formula 4′.
• in the reaction scheme 1, R1 and R2 are identical to or different from each other, and are each independently a hydrogen atom, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C1 to C30 heterocycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C1 to C30 heteroaryl group, or at least one of R1 and R2 is further coupled with a carbon atom adjacent to a carbon atom linked therewith to form a substituted or unsubstituted fused C6 to C30 aryl group, or a substituted or unsubstituted fused C1 to C30 heteroaryl group,
• X is a carbon atom or a nitrogen atom,
• Y is a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom,
• Z is a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom,
• R is C1 to C9 alkyl group of or C6 to C14 aryl group, and
• E is an electrophile.