One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides

Abstract

A mild, efficient synthesis of sulfonyl fluorides from aryl and heteroaryl bromides utilizing palladium catalysis is described.

Triple‐Bond Directed Csp2−N Bond Formation with N‐Fluorobenzenesulfonimide as Aminating Source: One‐Step Transformation of Aldehydes into Amines

“…Due to the instability of allene fluoride species iii , it will reorganize to attain aromaticity and alkynyl group by removal of CsF. Further, the CsF triggers the exclusion of PhSO 2 F (confirmed by 19 F NMR spectroscopic analysis, see the Supporting Information) and gave intermediate v . Now, two pathways are possible; Path a leads to the formation of side‐product by release through 6‐endo dig cyclization.…”

Sulfonyl Fluorides (SFs): More Than Click Reagents?

“…There are various methods to prepare sulfonyl fluorides from different type of starting materials such as heteroaromatic thiols, sulfonic acid, sodium benzene sulfonate, sulfonyl hydrazide, bromo benzene, iodo benzene, benzenethiosulfonate, diaryl sulfides, aryl sulfonyl chlorides, and some other unconventional starting material (Figure ) . In addition, alkyl sulfonyl fluorides may be readily accessed from alkyl bromides and rongalite, or through an electrochemical process .…”

“…thiols, avoids using transition metals and harsh reaction conditions, but the reported method is restricted to heterocyclic compounds. Recent methods by the groups of Willis and Ball utilize palladium catalyzed synthesis of sulfonyl fluorides from commercial and affordable aryl halides and is beneficial for late stage functionalization. Another popular method for preparation of sulfonyl fluorides is via Halex reaction from commercially available sulfonyl chlorides , …”

Benzothiazole Sulfinate: A Sulfinic Acid Transfer Reagent under Oxidation-Free Conditions

“…They can be converted to sulfones, 1–5 sulfonamides, 5–7 and sulfonyl fluorides, 3,8 which are found in natural products, 9 pharmaceuticals, 10–13 and materials 14,15 and used for bioconjugation. 16,17 Classically, sulfinic acids are synthesized via oxidation of thiols using H 2 O 2 or by the reduction of sulfonyl chlorides (Scheme 1A).…”