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Construction of Silicon-Containing Seven-Membered Rings by Catalytic [4 + 2 + 1] Cycloaddition through Rhodium Silylenoid
Organic Letters ( IF 5.2 ) Pub Date : 2020-04-02 , DOI: 10.1021/acs.orglett.0c00690
Ikuo Sasaki 1 , Toshimichi Ohmura 1 , Michinori Suginome 1
Affiliation  

A rhodium-catalyzed [4 + 2 + 1] cycloaddition involving 1,3-diene, alkyne, and silylene to afford silicon-containing seven-membered rings was established. In the presence of a rhodium catalyst bearing bis(diphenylphosphino)methane (DPPM), nona-1,3-dien-8-yne derivatives reacted efficiently at 80–110 °C with boryl(isopropoxy)silane or boryl(diethyamino)silane, which reacts as the synthetic equivalent of silylene, to afford 1-silacyclohepta-2,5-dienes (2,5-dihydro-1H-silepines). Regiodivergent and chemo- and stereoselective functionalization of the seven-membered nonconjugated diene was achieved by hydroboration mediated by Cs2CO3 or an iridium catalyst.

中文翻译:

硅基铑催化[4 + 2 +1]环加成反应制备含硅七元环

建立了铑催化的[4 + 2 + 1]环加成反应,该反应涉及1,3-二烯,炔烃和亚甲硅烷基,以提供含硅的七元环。在带有双(二苯基膦基)甲烷(DPPM)的铑催化剂的存在下,壬基1,3-三烯-8-炔衍生物在80–110°C下与硼基(异丙氧基)硅烷或硼基(二乙氨基)硅烷有效反应,其作为亚甲硅烷基的合成当量反应,得到1-silacyclohepta-2,5-二烯(2,5-二氢-1 H-西勒平)。七元非共轭二烯的区域发散性和化学和立体选择性官能化是通过Cs 2 CO 3或铱催化剂介导的硼氢化作用实现的。
更新日期:2020-04-24
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