Construction of seven- and eight-membered carbocycles by Lewis acid catalyzed C(sp³)–H bond functionalization

Abstract

Concise construction of seven- or eight-membered carbocycles was accomplished by Lewis acid catalyzed C(sp3)–H bond functionalization.

Facile Construction of 3,4‐dihydro‐2H‐1,2,4‐Benzothiadiazine 1,1‐Dioxides via Redox‐Neutral Cascade Condensation/[1,7]‐Hydride Transfer/Cyclization

“…for elegant construction of eight‐membered carbocycle‐fused piperidines with excellent diastereoselectivities, in which, double C(sp 3 )−H bonds were functionalized highly efficiently in one pot [21a] . Soon after that, the same group reported a concise construction of eight‐membered carbocycles via Lewis acid catalysed [1,7]‐hydride shift/cyclization process in good chemical yields [24b] . These two reactions, however, both still suffered from the drawbacks such as tedious preparation of substrates and employment of transitional metallic catalysts.…”

Diastereoselective Bidirectional C(sp3)−H Bond Functionalization of Piperazine Compounds

“…It is well developed for the construction of C−C, [5] C−O [5b,6] or C−N [7] bonds and offers rapid access to polycyclic compounds. [1,n]‐HT/cyclization occurs under either thermal conditions [7b] or the catalysis of Lewis acids [5c,e,8] and Brønsted acids [5d,7c,9] …”

A Comprehensive Account of Synthesis and Biological Activities of α‐lidene‐ Benzocycloalkanones and Benzoheterocycles

“…The authors described the procedure for the synthesis of various [1,4]thiazino [4,3-a] indole derivatives by using (ClCF 2 CO 2 Na) and S 8 as the difluoromethylthiolating agent under the basic condition with TEMPO as the oxidant (Table 3). In the sequential transformation process, four bonds were created selectively: one carbon-nitrogen, two carbon-sulfur, and one carbon-carbon bond, respectively (Scheme 26).…”

“…Scheme 26. Formation of [1,4]thiazino [4,3-a] indole from difluoromethylthiolating agent under a basic condition with TEMPO as oxidant at 70 °C.…”