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The first example of tetrazole‐directed meta‐selective C‐H nitration is described. This transformation provided a straightforward approach for the synthesis of biologically important m‐nitroaryltetrazoles in moderate to excellent yields with good functional group compatibility. In addition, new metallo‐β‐lactamase inhibitors were obtained by further transformation of the synthesized m‐nitroaryltetrazoles.
An unprecedented copper‐catalyzed regio‐ and stereoselective hydrodifluoroallylation of terminal alkynes was disclosed. This reaction employs easily available 3‐bromo‐3,3‐difluoropropene (BDFP) as the difluoroallylating reagent and 1,1,3,3‐tetramethyldisiloxane (TMDSO) as the hydride source, affording a variety of (E)‐1,1‐difluoro‐1,4‐dienes in moderate to good yields. The synthetic utility of this protocol has been demonstrated through the transformation of resulting (E)‐1,1‐difluoro‐1,4‐diene to difluoromethylated and trifluoromethylated derivatives.
The synthetic methodology for direct indole functionalizations is of great significance in indole chemistry and has been intensively investigated in the last few decades. From the perspective of green chemistry, oxygen is the best choice as the terminal oxidant in molecular synthesis. Hence, aerobic oxidative functionalization of indoles became a hot research topic in the last decade. Numerous efficient protocols in this field have been discovered that enable facile and efficient transformations of indoles to related valuable compounds, which are summarized and discussed in detail in this review.
A palladium(II)‐catalyzed cascade approach was established for the synthesis of indeno[1,2‐c]isochromen‐5(11H)‐ones starting from 2‐alkynyl tert‐butyl benzoates bearing a pendant α,β‐unsaturated carbonyl moiety in high yields (up to 99%) under mild conditions.
Reported is the condensation between o‐arylenediamines and nitroarenes enabled by a cooperative action of acid and base, providing a direct entry to 2‐aryl‐2H‐benzotriazoles. The potential practicability of this methodology was demonstrated by 100 mmol‐scale reactions and the synthesis of serotonin/dopamine receptor ligand and human growth hormone.
Iron‐mediated radical cyanoalkylsulfonylation/arylation of active olefins with cycloketone oxime derivatives via cleavage of C–C single bond and insertion of SO2 is developed for the preparation of cyanoalkylsulfonylated oxindoles. This difunctionalization of carbon–carbon double bond via a radical pathway involves cyclobutanone oxime ester fragmentation, sulfonyl radical generation and radical addition/5‐exo cyclization. The methodology displays good functional group tolerance and does not require any external bases or oxidants.
The first example of a [4+3]‐annulation reaction between in situ‐generated azaoxyallyl cations and isatoic anhydride has been developed for the construction of seven‐membered 1,4‐benzodiazepinediones in moderate to good yields (up to 91% yield). This annulation reaction involves the cascade reaction of decarboxylative addition of hexafluoroisopropanol to isatoic anhydride, addition to the azaoxyallyl cation, and intramolecular substitution to yield 1,4‐benzodiazepinediones.
Abstract. We have identified a switchable Prins cyclization process to form indoline‐fused tetrahydrofurans and indole‐fused oxepanes by applying different types of aldehydes under two sets of optimized conditions. Significantly, a novel Prins reaction mechanism involving an oxonium‐mediated rearrangement in the formation of five‐membered cyclic ethers is realized for the first time.
Abstract: Since the beginning of this century, homogeneous gold‐catalyzed alkyne transformations have been an active area of research in pursuit of developing novel and efficient synthetic methodologies. This emerging area of research which at the beginning exploited the mild Lewis acid character of gold and its propensity to form π‐complex with alkyne, has been reinvigorated upon the discovery of gold‐catalyzed oxidative alkyne functionalization in 2007. The gold‐catalyzed alkyne oxidation enabled direct access to α‐oxo gold carbenes and gold alkynal complex with versatile reactivity which has been applied to achieve novel transformations including but not limited to oxyarylation, C−H, X−H (X = N, O) insertion, cyclization, cycloaddition,
Abstract. A highly regio‐ and stereoselective oxyalkenylation of phosphinyl allenes is revealed for the first time. This protocol, merging visible light photoredox and palladium catalysis, provides a direct approach to conjugated tertiary allylic alcohol derivatives with broad functional group tolerance in moderate to excellent yields. Mechanistic studies suggest that, although two possible pathways exist in the transformation, radical oxyalkenylation promoted by visible light photoredox takes over the major pathway.
Abstract. A tandem phospha‐Michael addition/N‐acylation/intramolecular Wittig reaction of in situ formed aza‐o‐QMs is disclosed. This approach features high functional group tolerance and provides a convenient and practical access to biologically significant indole derivatives (37 examples, up to 91% yield) under mild reaction conditions.
A photoredox‐catalyzed defluoroborylation of. trifluoromethyl alkenes with N‐heterocyclic carbene. boranes is described for the synthesis of gemdifluoroallylboranes. This protocol exhibits a broad. substrate scope and good functional group compatibility,. which enables the late‐stage functionalization of. structurally complex compounds. Further transformations. of the defluoroborylation products to valuable CF2‐. containing molecules are also demonstrated.
Axially chiral hexatomic N‐heterobiaryls are among the most important class of structures with extensive utility in asymmetric catalysis as chiral ligands and organocatalysts, as exemplified by QUINAP and QUINOX. Besides, these atropisomers have attracted broad attention due to their application in drug discovery. Hence, it is not surprising that extensive efforts have been devoted for the pursue of efficient catalytic asymmetric methods for their direct and atroposelective construction. In addition to the direct heteroaryl‐aryl cross‐coupling, which remains as a challenge, a series of creative catalytic asymmetric strategies based on pre‐formed heterobiaryl systems have been developed by taking advantage of the intrinstic property of N ato.
A series of neutral iridium(I) complexes of the general type [(WCA‐NHC)]IrL(COD)] (COD = 1,5‐cyclooctadiene; L = phosphine, pyridine), bearing anionic N‐heterocyclic carbenes (WCA‐NHC) with a weakly coordinating anionic (WCA) borate moiety, were prepared by addition of phosphines and pyridine to [(WCA‐NHC)]Ir(COD)], in which the available coordination site is stabilized by intramolecular metal‐arene interaction (π‐face donation).
Abstract. The compounds like amides, carbamates, oxamates, oxamides, α‐keto amides, diketones, esters, ureas, etc. find extensive applications in pharmaceuticals, agrochemicals and organic synthesis. The classical syntheses of these compounds often involve cumbersome routes involving toxic chemicals. The carbonylation reactions such as aminocarbonylation, alkoxycarbonylation, oxidative carbonylation and double carbonylation deliver as an efficient and attractive alternative to the conventional synthetic routes even at industrial scale. The catalytic single carbonylation reactions are extensively studied, however, catalytic double carbonylation reactions are not explored for several potential applications. This review covers literature on th.
A pyridyl group‐assisted palladium‐catalyzed secondary C(sp3)‐H arylation protocol was developed. A substituent at the 3‐position of the pyridyl group is proved to be important for promoting C‐H arylation and controlling the regioselectivity. Aryl iodides can be used as coupling partners. The reaction proceeded in good to excellent yields with good functional group tolerance, even on the gram‐scale. The preliminary asymmetric reaction was investigated using an L‐proline derivative as a chiral ligand.
Abstract. With ethylene glycol as a green solvent, a general transition metal‐free photocatalytic system using 9‐mesityl‐10‐methylacridinium perchlorate (Acr+−Mes ⋅ ClO4−) as catalyst was developed for the synthesis of sulfone‐containing heterocycles including thioflavones, oxindoles, and quinoline‐2,4(1H,3H)‐diones through the cascade sulfonation/cyclization reactions under the irradiation of blue light at room temperature.
The first palladium‐catalyzed direct C(sp3)‐H chalcogenation of benzylics with diaryl disulfides and diselenide has been established. The coupling reaction proceeds between the thioether radical and palladiumcycle intermediate. Picolinamides serve as an excellent directing group for the C‐H activation of benzylic methyls and can be easily removed. The current protocol exhibits a relatively broad substrate scope and high functional group compatibility. A mechanistic study indicates that palladium(III) intermediate is probably formed during the course of the reaction.
A silver(I)‐ and base‐mediated 1,3‐dipolar [4+3] cycloaddition reaction of in situ generated 1,2‐diaza‐1,3‐dienes with in situ formed C,N‑cyclic azomethine imines has been developed. This protocol provided a novel and efficient method for the synthesis of biologically important 1,2,4,5‐tetrazepine derivatives with a wild substrate scope and excellent functional group tolerance in moderate to excellent yields.

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