2022
DOI: 10.1039/d2cc03234a
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Regulable cross-coupling of alcohols and benzothiazolesviaa noble-metal-free photocatalyst under visible light

Abstract: Here, we realize a regulable cross-coupling reaction using alcohols as alkylating reagents to functionalize benzothiazoles. Two types of cross-coupling products are obtained with the highest isolated yields of up to...

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Cited by 8 publications
(4 citation statements)
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“…Heterocyclic compounds containing S atoms and their derivatives, such as benzothiazole, are also very important in organic synthesis. Our group previously reported the synthesis of alkylated benzothiazole derivatives from alcohols as alkylating agents, 19 and here, we were surprised to find that the present reaction conditions were also applicable to the synthesis of alkylated benzothiazoles ( 8c ). Many cross-coupling-useful functional groups, such as cyano ( 9c ), chloro ( 10c–11c ), fluoro ( 12c ), methyl ( 13c ), and ether ( 14c–15c ) groups were all compatible and achieved moderate to good yields.…”
mentioning
confidence: 58%
“…Heterocyclic compounds containing S atoms and their derivatives, such as benzothiazole, are also very important in organic synthesis. Our group previously reported the synthesis of alkylated benzothiazole derivatives from alcohols as alkylating agents, 19 and here, we were surprised to find that the present reaction conditions were also applicable to the synthesis of alkylated benzothiazoles ( 8c ). Many cross-coupling-useful functional groups, such as cyano ( 9c ), chloro ( 10c–11c ), fluoro ( 12c ), methyl ( 13c ), and ether ( 14c–15c ) groups were all compatible and achieved moderate to good yields.…”
mentioning
confidence: 58%
“…The authors have cited additional references within the Supporting Information (Ref. [16][17][18][19][20][21][22][23][24][25][26][27][28][29][30]).…”
Section: Discussionmentioning
confidence: 99%
“…We also applied 1,2-Diphenoxyethane (DPE) to capture the radical during the homogeneous tests (Figure S35), and there is an obvious peak centered at ~3505 G in spectra from both acidic and neutral media, which provides further evidence for the proposed radical mechanism. [40] Therefore, when it comes to the COP, the SET process between 2N with radical (2N-R) and Cl À is quickly carried out.…”
Section: Mechanism Study Via Experimentsmentioning
confidence: 99%