Hypervalent iodine promoted the synthesis of cycloheptatrienes and cyclopropanes

Abstract

A new strategy is reported for intramolecular Buchner-type reactions using PIDA as a promotor. Traditionally, the Buchner reaction is achieved via Rh-carbenoids derived from RhII catalysts with diazo compounds. Herein,...

Recent Updates on Electrogenerated Hypervalent Iodine Derivatives and Their Applications as Mediators in Organic Electrosynthesis

“…In 2022, Wright, Wen, Zhang, and co-workers reported one example of cation-induced [2 + 1] cyclization of alkenyl amide mediated by electrochemically generated iodine (III) intermediate ( Yuan et al, 2022 ). The iodine (III) species 1b , which in situ generated from iodobenzene in the presentence of n-Bu 4 NOAc in HFIP, smoothly promoted the annulation process and constructed highly strained cyclopropane-fused lactam in 72% yield ( Scheme 2L ).…”

Electrochemically-promoted synthesis of benzo[b]thiophene-1,1-dioxides via strained quaternary spirocyclization

“… 16 Hence, our interest in electrochemical transformation and green chemistry prompts us to develop a new strategy for the direct formation of such benzothiophene motifs via an alkenyl radical intermediate followed by the selective ipso -addition instead of the ortho -attack pathway, which underwent S-migration via more strained quaternary spirocyclization ( Scheme 1e ). 17 …”

Electrochemically Promoted [3 + 2] Annulation of Imidazo[1,2-a]pyridine with Alkynes

“…The twofold C–H bond activation strategy under electrochemical conditions needs to be further explored. In a continuation of our efforts in electrochemical synthesis and green chemistry, we also recently reported a practical protocol for the [4 + 2] annulation of arenes with alkynes . Additionally, we found that mild electrochemical conditions could be used to achieve a practical Rh­(III)-catalyzed [3 + 2] annulation product, which could act as the organic small molecule for the chemical doping of perovskite .…”