An unprecedented nickel-catalyzed reductive 1,2-dialkynylation of alkenes bearing an 8-aminoquinoline directing group has been developed. This method proceeded through a migratory insertion/reductive-coupling process under mild conditions with a wide substrate scope and good functional group tolerance, providing direct access to the synthetically flexible 1,5-diynes. Moreover, the 1,2-dialkynylation products could be further converted to borate-ester- or azide-functionalized 1,5-dienes, ditriazole, β-diyne primary amide, and trisubstituted benzene.

The activation and functionalization of C−F bonds for the construction of C−C and C−X bonds have drawn significant research attention in recent years. However, the chemoand stereoselective control of dual C−F bond functionalization of gem-difluoroalkenes remains a formidable challenge. Herein, a Nicatalyzed reductive cross-coupling of gem-difluoroalkenes with alkenyl-electrophiles and D 2 O that allowed the generation of C(sp 2 )−C(sp 2 ) bonds and C(sp 2 )−D bonds in one pot by successive defluorination is described. This methodology offers facile access to various deuterated 1,3-dienes with broad functional group compatibility and (E)-selectivity under mild conditions. Preliminary mechanistic studies indicate that α-alkenyl-substituted monofluoroalkenes might be intermediates in this protocol.

A palladium-catalyzed asymmetric C−C bond activation/carbonylation of cyclobutanones with CO has been developed. This reaction provided an efficient method for the synthesis of chiral indanones bearing a quaternary carbon stereocenter in good yields with an excellent enantiomeric ratio, exhibiting good functional group tolerance. Transformations of the products to chiral 3,4-dihydroquinolin-2(1H)-one and 1H-indene further demonstrated the versatility of this reaction.T ransition-metal-catalyzed carbonylation with carbon monoxide (CO) serves as a powerful tool for the rapid access to carbonylated compounds, 1,2 which has been widely employed as a key step for the synthesis of natural products and bioactive molecules. 3 Recently, Pd-catalyzed asymmertric cascade Heck/carbonylation of terminal alkenes described by Correia and co-workers, 4 Zhu and co-workers, 5 Zhang and coworkers, 6 and Guan and co-workers 7 provided convenient methods for the construction of chiral oxindoles, spirooxindoles, dihydrobenzofurans, and 3,4-dihydroisoquinolinones (Scheme 1a). Our group realized a Pd-catalyzed asymmertric Heck/carbonylation/desymmetrization of cyclopentenes to access bicyclo[3.2.1]octanes with a three chiral carbon stereocenter in good efficiency (Scheme 1b). 8a Moreover, we also developed Pd-catalyzed enantioselective dearomative carbonylation of indoles and carbamoyl/carbonylation of tethered alkenes to assemble polycyclic indolines and γ-

Phenolic compounds are the most ubiquitously distributed pollutants, and are highly toxic to living organisms, however the detailed mechanism how phenols exert toxic effects remains elusive. Here, Escherichia coli and phloroglucinol are adapted as proxy to elucidate the molecular mechanism of phenols' toxicity. We demonstrated that phloroglucinol complexed with iron and promoted the generation of hydroxyl radicals in Fenton reaction, leading to reducing power depletion and lipid peroxidation, and further leading to ferroptosis-like cell death of E. coli. This ferroptotic death can be triggered by various phenols in diverse organisms, from bacteria to mammalian cells. Furthermore, we demonstrated that phloroglucinol-induced ferroptosis suppressed tumor growth in mice effectively, indicating phloroglucinol as promising drug for therapy-resistant cancers. It's also discovered that repression of this ferroptosis-like cell death benefited microbial degradation or production of desired phenolic compounds, showing great application potential in biotechnology field.