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Visible‐Light‐Mediated Nitrogen‐Centered Radical Strategy: Preparation of 3‐Acylated Spiro[4,5]trienones

A nitrogen-centered radical strategy for the preparation of 3-acylated spiro[4,5]trienones via visible-light-mediated acylation/ipso-cyclization of alkynes with acyl oxime esters is reported. The alkyl- and aryl-substituted acyl radicals, which generate from the cleavage of carbon-carbon σ-bonds in acyl oxime esters via nitrogen-centered radical pathway,...

1,3‐Difunctionalization of Imino‐Carbenes via Rhodium‐Catalyzed Reactions of Triazoles with Acyl Selenides

Herein, we report on the rhodium-catalyzed reaction of triazoles with acyl selenides. Under thermal reaction conditions and in the presence of a rhodium catalyst, a rapid 1,3-difunctionalization reaction occurs to provide valuable α-seleno enamides with high stereoselectivity and broad functional group tolerance, which was demonstrated in 35 examples...

Sulfoxide‐Controlled Stereoselective Aza‐Piancatelli Reaction

The development of a novel stereoselective aza-Piancatelli reaction to access 4-aminocyclopentenones is reported. This transformation relies on the use of chiral o-sulfinyl anilines as chiral inductors to afford the targeted products in good to excellent yields. Remarkably, the high value-added cyclopentenones could be obtained in excellent drs (up...

B(C6F5)3‐Catalyzed Hydroarylation of Terminal Alkynes with Phenols

Abstract We developed a B(C6F5)3 catalyzed hydroarylation of terminal alkynes with various phenols at room temperature without adding any additives, leading to the synthesis of 2-gem-vinylphenols with good regio-selectivity. Those transformations featured a broad substrate scope with moderate yields. Mechanism studies indicated that those transformations...

Diastereoselective Synthesis of oxa‐Bridged Tetracyclic Benzooxazines from the Reaction of 2‐Isocyanophenyloxyacrylates and Propargylic Esters

Abstract A cascade annulation of 2-isocyanophenyloxyacrylate and propargylic ester under basic conditions has been disclosed. This methodology enables diastereoselective synthesis of oxa-bridged tetracyclic benzooxazine. The annulation proceeds through isomerization, Michael addition, triple annulation and acyl migration processes.

Markovnikov Wacker‐Tsuji Oxidation of Allyl(hetero)arenes and Application in a One‐Pot Photo‐Metal‐Biocatalytic Approach to Enantioenriched Amines and Alcohols

Abstract The Wacker-Tsuji aerobic oxidation of various allyl(hetero)arenes under photocatalytic conditions to form the corresponding methyl ketones is presented. By using a palladium complex [PdCl2(MeCN)2] and the photosensitizer [Acr-Mes]ClO4 in aqueous medium and at room temperature, and by simple irradiation with blue led light, the desired carbonyl...

Visible Light‐Mediated Synthesis of Se−S Bond‐Containing Peptides

Abstract A visible light-initiated method has been developed for preparation of Se−S bond-containing peptides. The method is based on generation of sulfur-centered radical employing organic dye. The protocol is tolerant to unprotected peptides with “sensitive” amino acids. The stability of Se−S bond is evaluated in buffers at different pH (3.0–10.0)...

Metal‐Catalyzed Reactivity Reversal in the Sulfonylation Reaction of α‐Allenols: Controlled Synthesis of 4‐(Arylsulfonyl)‐2,5‐Dihydrofurans

Abstract The synergy between metal catalysis and radical chemistry allows to surpass previous limitations of the reactions between allenols and sulfonylating reagents. Considering that previous studies of the reactivity of the allenol moiety with sulfonylating reagents have been limited to addition and rearrangement reactions lacking cyclization, we...

Direct Use of Benzylic Alcohols for Multicomponent Synthesis of 2‐Aryl Quinazolinones Utilizing the π‐Benzylpalladium(II) System in Water

Abstract We demonstrate the direct use of benzylic alcohols for a multicomponent reaction of readily available isatoic anhydrides with amines in water, which is a synthetic route for the direct construction of a series of 2-aryl quinazolinones. This one-pot synthetic method involves the dehydrative N-benzylation of in situ generated anthranilamides...

Visible Light Mediated Synthesis of Oxindoles

Abstract Functionalized oxindoles are privileged heterocyclic scaffolds and common core structural motifs that are broadly present in numerous natural products and serve as key intermediates in the synthesis of biological products, agrochemicals, and pharmaceuticals. Oxindoles exhibit a broad pharmacological and physiological activities, and diverse...

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