2011 Fiscal Year Final Research Report
Efficient Nucleophilic Addition to Haloacetylenes and Its Application
| Project/Area Number |
22655014
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| Research Category |
Grant-in-Aid for Challenging Exploratory Research
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| Allocation Type | Single-year Grants |
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| Research Field |
Organic chemistry
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| Research Institution | Tokyo Institute of Technology |
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Principal Investigator |
URABE Hirokazu 東京工業大学, 大学院・生命理工学研究科, 教授 (10176745)
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| Project Period (FY) |
2010 – 2011
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| Keywords | インドール / 求核付加反応 / スルホンアミド / テトラヒドロフラン / パラジウム / ハロアルキン / ピロール / ヘテロ環化合物 |
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| Research Abstract |
When imidazolines, imidazoles, N-allyl-, N-aryl-, or N-propyl-sulfonamides were heated with 1-halo-1-alkynes in DMF, cis-2-hetero groupsubstituted-1-halo-1-alkenes were produced with high regioand stereoselectivities. On treatmen with Pd catalysts, the sulfonamide adducts were led to pyrroles, indoles, and benzothiazine 1, 1-dioxides. Similarly, when amines or alcohols were heated with 1-halo-1-alkynes in DMF, their nucleophilic addition to 1-halo-1-alkynes resulted in the generation of vinyl carbene intermediates, which were intercepted with sodium sulfinate to give 2-hetero group-substituted-1-sulfonyl-1-alkenes.
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Research Products
(14 results)
