Differential Dihydrofunctionalization: A Dual Catalytic Three-Component Coupling of Alkynes, Alkenyl Bromides, and Pinacolborane.
Differential Dihydrofunctionalization: A Dual Catalytic Three-Component Coupling of Alkynes, Alkenyl Bromides, and Pinacolborane.
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DOI：
10.1002/anie.202206462
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发表时间：
2022-09-12
影响因子：
16.6
通讯作者：
Lalic, Gojko
中科院分区：
文献类型：
--
作者：
Baumann, James E.;Lalic, Gojko
一种新的末端炔烃二氢功能化新方法可以通过末端炔烃、烯基溴化物和频那多硼烷的还原三组分偶联反应来合成烯丙基硼酸酯。铜/钯催化体系的协同作用促进了该转化，并导致了炔的两个π-键的氢化官能化。烯丙基硼酸酯的合成可以在多种官能团的存在下完成，这些官能团包括酯、腈、卤代烷、磺酸酯、缩醛、受保护的末端炔、芳基卤化物和硅醚。力学实验揭示了微妙的配体效应对钯催化剂性能的重要性。一种新的末端炔烃二氢功能化新方法可以通过末端炔烃、烯基溴化物和频那多硼烷的还原三组分偶联反应来合成烯丙基硼酸酯。铜/钯催化体系的协同作用促进了该转化，并导致了炔的两个π-键的氢化官能化。
A new method for differential dihydrofunctionalization of terminal alkynes enables the synthesis of allylic boronate esters through reductive three-component coupling of terminal alkynes, alkenyl bromides, and pinacolborane. The transformation is promoted by cooperative action of a copper/palladium catalyst system and results in hydrofunctionalization of both π-bonds of an alkyne. The synthesis of allylic boronate esters can be accomplished in the presence of a wide range of functional groups, including, esters, nitriles, alkyl halides, sulfonyl esters, acetals, protected terminal alkynes, aryl halides, and silyl ethers. Mechanistic experiments reveal the importance of subtle ligand effects on the performance of the palladium co-catalyst. A new method for differential dihydrofunctionalization of terminal alkynes enables the synthesis of allylic boronate esters through reductive three-component coupling of terminal alkynes, alkenyl bromides, and pinacolborane. The transformation is promoted by cooperative action of a copper/palladium catalyst system and results in hydrofunctionalization of both π-bonds of an alkyne.
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影响因子：
15
作者：
Hazra A;Kephart JA;Velian A;Lalic G
通讯作者：
Lalic G
影响因子：
37.8
作者：
Gao, De-Wei;Gao, Yang;Engle, Keary M.
通讯作者：
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影响因子：
15
作者：
HALPERN, J;JAMES, BR;KEMP, ALW
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KEMP, ALW
影响因子：
4.3
作者：
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通讯作者：
Cheng, Chien-Hong
影响因子：
15
作者：
Hazra, Avijit;Chen, Jason;Lalic, Gojko
通讯作者：
Lalic, Gojko