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1.
Org Biomol Chem ; 22(6): 1186-1193, 2024 Feb 07.
Article in English | MEDLINE | ID: mdl-38214570

ABSTRACT

An azido-radical-triggered cyclization of N-(o-cyanobiaryl)acrylamides with TMSN3via a C(sp3)-N/C(sp2)-C(sp3)/C(sp2)-N bond formation cascade is described. This reaction features mild conditions and high bond-forming efficiency, making it an efficient method for the construction of azide-substituted pyridophenanthridines.

2.
Org Lett ; 25(40): 7412-7416, 2023 Oct 13.
Article in English | MEDLINE | ID: mdl-37788358

ABSTRACT

A visible-light-promoted cascade cyclization of 3-ethynyl-[1,1'-biphenyl]-2-carbonitriles with unsaturated α-bromocarbonyls for the synthesis of tetrahydrobenzo[mn]cyclopenta[b]acridines is described. Three C(sp3)-C(sp2) bonds, one C(sp2)-N bond, and three cycles can be formed in a single reaction through the addition of a C-centered radical to the carbon-carbon triple bond and three radical cyclizations. This reaction features mild conditions, wide substrate scope, and high bond-forming efficiency.

3.
J Org Chem ; 88(7): 4528-4535, 2023 Apr 07.
Article in English | MEDLINE | ID: mdl-36913662

ABSTRACT

A copper-catalyzed cascade multicomponent reaction for synthesizing ditriazolyl diselenides from azides, terminal alkynes, and elemental selenium has been developed. The present reaction features utilizing readily available and stable reagents, high atom-economy, and mild reaction conditions. A possible mechanism is proposed.

4.
Org Lett ; 25(3): 517-521, 2023 Jan 27.
Article in English | MEDLINE | ID: mdl-36649602

ABSTRACT

An oxidative dehydrogenative coupling of thiols with alkanes via direct C(sp3)-H bond functionalization to form a new C-S bond and S═O double bond was developed. The present reaction features the use of readily available reagents and high step- and atom-efficiency, thus providing an efficient access to sulfoxides. A possible mechanism is proposed.

5.
Org Lett ; 23(15): 6158-6163, 2021 Aug 06.
Article in English | MEDLINE | ID: mdl-34313448

ABSTRACT

A novel annulation of 2-cyanoaryl acrylamides via C═C double bond cleavage has been developed for facile and efficient access to a broad spectrum of functionalized 4-amino-2-quinolones, which are important N-heterocycles. In this transformation, the solvent THF is demonstrated to play a crucial role, and the addition of alkyl radicals to nitrile, 1,5-hydride shift, and cleavage of the C-C bond are involved in the mechanism.

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