Palladium-Catalyzed Silylation of 2,3-Allenols with Unactivated Disilanes: Access to 2-Silyl-1,3-butadienes and α-Silyl-β-hydroxy Vinylsilanes

被引：7
|
作者：
Xu, Guang-Li [1 ,2 ]
Wang, Zhong-Xia [1 ,2 ,3 ]
机构：
[1] Univ Sci & Technol China, CAS Key Lab Soft Matter Chem, Hefei 230026, Anhui, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
[3] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300072, Peoples R China
来源：
ORGANIC LETTERS | 2022年 / 24卷 / 02期
基金：
中国国家自然科学基金;
关键词：
ANIONIC-POLYMERIZATION; STEREOSELECTIVE-SYNTHESIS; EFFICIENT SYNTHESIS; REACTION CHEMISTRY; SILICON; COMPLEXES; MONOMERS; 1,3-BUTADIENES; 1,3-DIENES; ALLENES;
D O I：
10.1021/acs.orglett.1c04141
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Regioselective silylation of 2,3-allenols with disilanes was carried out under catalysis of Pd(2)dba(3)/P(o-MeOC6H4)(3). In the presence of Cs2CO3, the reaction achieved 2-silyl-1,3-dienes. Reaction of 1-aryl-2,3-allenols gave the products with excellent Z/E selectivity and E-isomers as the major species. Reaction of alpha-alkylallenols or alpha-alkyl-alpha-aryl-allenols resulted in products with moderate Z/E selectivity and E-isomers are also major. Without a base, the reaction produced alpha-silyl-beta-hydroxyl vinylsilanes, which were converted to 2-silyl-1,3-dienes upon treatment with Cs2CO3.
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收藏
页码：692 / 696
页数：5
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