A Heck-Matsuda Process for the Synthesis of β-Arylethenesulfonyl Fluorides: Selectively Addressable Bis-electrophiles for SuFEx Click Chemistry.
A Heck-Matsuda Process for the Synthesis of β-Arylethenesulfonyl Fluorides: Selectively Addressable Bis-electrophiles for SuFEx Click Chemistry.
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DOI：
10.1002/anie.201608807
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发表时间：
2016-11-02
影响因子：
16.6
通讯作者：
Sharpless, K. Barry
中科院分区：
文献类型：
--
作者：
Qin, Hua-Li;Zheng, Qinheng;Bare, Grant A. L.;Wu, Peng;Sharpless, K. Barry
关键词：
介绍了一种合成β-芳基乙烯磺酰氟的Heck-Matsuda方法。乙烯磺酰氟（即，乙烯基磺酰氟或ESF）在催化剂乙酸钯（II）存在下与稳定且容易制备的芳烃重氮四氟硼酸盐进行β-芳基化，以43-97%产率得到肉桂酰氟的E-异构体磺酰基类似物。发现β-芳基乙烯磺酰氟是用于硫（VI）氟化物交换（SuFEx）点击化学的选择性可寻址的双亲电体，其中烯基部分或磺酰氟基团可以是在限定条件下亲核攻击的唯一位点，使得这些相当简单的核对于共价药物发现具有吸引力。介绍了一种合成β-芳基乙烯磺酰氟的Heck-Matsuda方法。乙烯磺酰氟（即，乙烯基磺酰氟或ESF）在催化剂乙酸钯（II）存在下与稳定且容易制备的芳烃重氮四氟硼酸盐进行β-芳基化，以43-97%产率得到肉桂酰氟的E-异构体磺酰基类似物。发现β-芳基乙烯磺酰氟是用于硫（VI）氟化物交换（SuFEx）点击化学的选择性可寻址的双亲电体，其中乙烯基部分或磺酰氟基团可以是在限定条件下亲核攻击的唯一位点，使得这些相当简单的核对于共价药物发现具有吸引力。
A Heck-Matsuda process for the synthesis of the otherwise difficult to access compounds, β-arylethenesulfonyl fluorides, is described. Ethenesulfonyl fluoride (i.e., vinylsulfonyl fluoride, or ESF) undergoes β-arylation with stable and readily prepared arenediazonium tetrafluoroborates in the presence of the catalyst palladium(II) acetate to afford the E-isomer sulfonyl analogues of cinnamoyl fluoride in 43–97% yield. The β-arylethenesulfonyl fluorides are found to be selectively addressable bis-electrophiles for sulfur(VI) fluoride exchange (SuFEx) click chemistry, in which either the alkenyl moiety or the sulfonyl fluoride group can be the exclusive site of nucleophilic attack under defined conditions, making these rather simple cores attractive for covalent drug discovery. A Heck-Matsuda process for the synthesis of the otherwise difficult to access compounds, β-arylethenesulfonyl fluorides, is described. Ethenesulfonyl fluoride (i.e., vinyl sulfonyl fluoride, or ESF) undergoes β-arylation with stable and readily prepared arenediazonium tetrafluoroborates in the presence of the catalyst palladium(II) acetate to afford the E-isomer sulfonyl analogues of cinnamoyl fluoride in 43–97% yield. The β-arylethenesulfonyl fluorides are found to be selectively addressable bis-electrophiles for sulfur(VI) fluoride exchange (SuFEx) click chemistry, in which either the vinyl moiety or the sulfonyl fluoride group can be the exclusive site of nucleophilic attack under defined conditions, making these rather simple cores attractive for covalent drug discovery.
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DOI：
10.1039/j39680000992
发表时间：
1968-01-01
期刊：
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC
影响因子：
--
作者：
CULBERTSON, BM;DIETZ, S
通讯作者：
DIETZ, S
影响因子：
3.6
作者：
Kim, Dong Wook;Jeong, Hwan-Jeong;Chi, Dae Yoon
通讯作者：
Chi, Dae Yoon
影响因子：
3.6
作者：
Chinthakindi, Praveen K.;Kruger, Hendrik G.;Arvidsson, Per I.
通讯作者：
Arvidsson, Per I.
影响因子：
3.6
作者：
BIANCHI, TA;CATE, LA
通讯作者：
CATE, LA
影响因子：
16.6
作者：
Dong, Jiajia;Sharpless, K. Barry;Kwisnek, Luke;Oakdale, James S.;Fokin, Valery V.
通讯作者：
Fokin, Valery V.