The use of phosphine ligands to control the regiochemistry of Pd-catalyzed hydrostannations of 1-alkynes:: Synthesis of (E)-1-tributylstannyl-1-alkenes

The use of phosphine ligands to control the regiochemistry of Pd-catalyzed hydrostannations of 1-alkynes:: Synthesis of (E)-1-tributylstannyl-1-alkenes
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DOI:
10.1021/ol702982x
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发表时间:
2008-03-06
期刊:
影响因子:
5.2
通讯作者:
Chong, J. Michael
Chong, J. Michael
中科院分区:
化学1区
文献类型:
--
作者:
Darwish, Alla;Lang, Adam;Chong, J. Michael

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配体效应对钯催化的末端炔氢锡化反应的区域化学影响很大。使用诸如Cy(3)P、t-Bu(2)PCH(2)t-Bu和t-Bu(3)P等膦,对于通常使用的Ph(3)P显示较低区域选择性的底物,可提供区域选择性高达bbb99:< 1的(E)-1-三丁基锡基-1-烯烃。
The regiochemistry of palladium-catalyzed hydrostannations of terminal alkynes is dramatically influenced by ligand effects. Use of phosphines such as Cy(3)P, t-Bu(2)PCH(2)t-Bu, and t-Bu(3)P provides (E)-1-tributylstannyl-1-alkenes with regioselectivities up to > 99:< 1 for substrates where the commonly used Ph(3)P shows much lower regioselectivities.