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1.
J Org Chem ; 89(12): 8804-8814, 2024 Jun 21.
Article in English | MEDLINE | ID: mdl-38860924

ABSTRACT

1,4-/1,3-Regioselective bifunctionalization of 1,3-enynes with selenosulfonates in water under catalyst-free conditions for the construction of sulfonyl allene and 1,3-disulfonyl-conjugated dienes respectively have been developed. The reactions feature mild reaction conditions in aqueous solution and remarkable regioselectivity controlled by substrates.

2.
Org Lett ; 25(10): 1776-1781, 2023 Mar 17.
Article in English | MEDLINE | ID: mdl-36867002

ABSTRACT

Herein, we provide a novel method for the synthesis of 1,3-dibenzenesulfonylpolysulfane (DBSPS), which further reacts with boronic acids to afford thiosulfonates. Commercially available boron compounds greatly expanded the range of thiosulfonates. Experimental and theoretical mechanistic investigations suggested that DBSPS could provide both thiosulfone fragments and dithiosulfone fragments, but the generated aryl dithiosulfonates were unstable and decomposed into thiosulfonates.

3.
J Org Chem ; 88(2): 828-837, 2023 Jan 20.
Article in English | MEDLINE | ID: mdl-36577098

ABSTRACT

A photocatalytic synthesis of thieno[3,4-c]quinolin-4(5H)-ones/selenopheno[3,4-c]quinolin-4(5H)-ones using diphenyl disulfide or diphenyl diselenide as sulfur or selenium sources was developed. Two C-S/Se bonds and one C-C bond were constructed simultaneously without transition metals and other additives.

4.
Org Lett ; 23(21): 8246-8251, 2021 Nov 05.
Article in English | MEDLINE | ID: mdl-34652929

ABSTRACT

A visible-light-triggered radical cascade sulfonylation/aryl migration/desulfonylation and C-S/Se bond formation reaction of butenyl benzothiazole sulfone with thiosulfonates or selenosulfonates is developed. This study affords the 1,2,4-trifunctionalization of butenyl benzothiazole sulfone derivatives under mild conditions.

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