PIFA‐Mediated Cross‐Dehydrogenative Coupling of N‐Heteroarenes with Cyclic Ethers: Ethanol as an Efficient Promoter

Abstract

Ethanol is typically used in organic synthesis as an environmentally benign solvent. Herein, we report a mild and efficient cross-dehydrogenative coupling (CDC) reaction of N-heteroarenes with cyclic ethers by uncovering the new reactivity of ethanol as an efficient promoter in PIFA-mediated radical process. The reaction proceeds smoothly under the irradiation of visible light and features excellent functional group compatibility, which allows the expedite synthesis of a variety of medicinally valuable Cα-heteroarylated cyclic ethers in moderate to high yields.

A Novel PIFA/KOH Promoted Approach to Synthesize C2-arylacylated Benzothiazoles as Potential Drug Scaffolds

“…Finally, the oxidative dehydrogenation of D furnished the target product 3aa through the elimination of CF 3 COOH and PhI. The presence of the latter compound was detected in the reaction solution by GC-MS [ 44 , 45 ].…”

High‐Power Near‐Neutral Aqueous All Organic Redox Flow Battery Enabled with a Pair of Anionic Redox Species

“…On the cathode side, 4-(propoxy-3-sodium sulfonate)-2,2,6,6tetramethyl piperidin-1-yl)oxyl (PSS-TEMPO) was synthesized. Compared with the reported 4-CO 2 Na-TEMPO and 4-SO 3 K-TEMPO, [12] the longer side chain of PSS-TEMPO effectively alleviates the adverse impact of the strong electron-withdrawing group on the skeleton stability, and provides effective steric hindrance suppressing the interactions between TEMPO radicals, also ensuring a lower permeability through CEMs. An AORFB system compatible with CEMs at near-neutral conditions has been demonstrated by pairing (PPBPy)Br 2 and PSS-TEMPO, which presents a cell voltage as high as 1.61 V and the highest power density of 509 mW cm À 2 among all the reported pHneutral aqueous RFBs.…”

Transformations based on direct excitation of hypervalent iodine(iii) reagents

“…30 Recently, Zhang and Wang reported a system in which ethanol was used as a HAT catalyst allowing functionalization of C(sp 3 )-H bonds in different substrates. 31 Scheme 2 Examples of Minisci-type coupling with different radical precursors.…”