meta-C-H Arylation and Alkylation of Benzylsulfonamide Enabled by a Palladium(II)/Isoquinoline Catalyst.
meta-C-H Arylation and Alkylation of Benzylsulfonamide Enabled by a Palladium(II)/Isoquinoline Catalyst.
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DOI：
10.1002/anie.201704411
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发表时间：
2017-07-03
期刊：
影响因子：
--
通讯作者：
Yu JQ
中科院分区：
文献类型：
--
作者：
Cheng G;Wang P;Yu JQ
采用新开发的缺电子导向基团和异喹啉作为配体，实现了钯（II）催化的苄基磺酰胺间位C-H芳基化和烷基化反应。该方案具有底物范围广、官能团耐受性好等特点。间位取代的苄基磺酰胺可以通过Julia型烯化反应容易地转化为磺酸钠、磺酸酯、磺酰胺以及苯乙烯。异喹啉配体的独特影响强调了配体和导向基团之间微妙匹配的重要性。以异喹啉为配体，以2-甲氧羰基异喹啉（NBE-CO_2 Me）为过渡介质，实现了钯催化的苄基磺酰胺间位C-H芳基化和烷基化反应.该方案具有底物范围广、官能团耐受性好等特点。间位取代的苄基磺酰胺可以通过Julia型烯化反应容易地转化为磺酸钠、磺酸酯、磺酰胺以及苯乙烯。
Palladium(II)-catalyzed meta-C–H arylation and alkylation of benzylsulfonamide using 2-carbomethoxynorbornene (NBE-CO2Me) as a transient mediator are realized using a newly developed electron-deficient directing group and isoquinoline as a ligand. This protocol features broad substrate scope and excellent functional group tolerance. The meta-substituted benyzlsulfonamide can be readily transformed to sodium sulfonate, sulfonate ester, sulfonamide, as well as styrenes via Julia-type olefination. The unique impact of the isoquinoline ligand underscores the importance of subtle matching between ligands and the directing groups. Palladium(II)-catalyzed meta-C–H arylation and alkylation of benzylsulfonamide using 2-carbomethoxynorbornene (NBE-CO2Me) as a transient mediator are realized using isoquinoline as a ligand. This protocol features broad substrate scope and excellent functional group tolerance. The meta-substituted benyzlsulfonamide can be readily transformed to sodium sulfonate, sulfonate ester, sulfonamide, as well as styrenes via Julia-type olefination.
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