2012年2月
High Performance of N-Alkoxycarbonyl-imines in Triethylborane-Mediated Tin-Free Radical Addition
JOURNAL OF ORGANIC CHEMISTRY
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- 巻
- 77
- 号
- 3
- 開始ページ
- 1547
- 終了ページ
- 1553
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1021/jo2025042
- 出版者・発行元
- AMER CHEMICAL SOC
Triethylborane-mediated tin-free radical alkylation of N-alkoxycarbonyl-imines, such as N-Boc-, N-Cbz-, and N-Teoc-imines, proceeded smoothly at a low temperature (-78 to -20 degrees C) to give the corresponding adducts in high yield. Although the formation of isocyanate was the major unfavorable reaction at room temperature, a one-pot conversion of N-Boc-imine to N-ethoxycarbonyl-adduct was possible through the corresponding isocyanate generated in situ. The higher performance of N-alkoxycarbonyl-imine than those of N-Ts- and N-PMP-imines is rationalized by a moderate electron-withdrawing character of an alkoxycarbonyl group that makes both addition of alkyl radical and trapping of the resulting aminyl radical by triethylborane efficiently fast.
- リンク情報
- ID情報
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- DOI : 10.1021/jo2025042
- ISSN : 0022-3263
- eISSN : 1520-6904
- Web of Science ID : WOS:000300462700033