Synthesis of Polysubstituted 2-Iodoindenes via Iodonium-Induced Cyclization of Arylallenes
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- 作者：Charlotte Grandclaudon ; Véronique Michelet ; Patrick Y. Toullec
- 刊名：Organic Letters
- 出版年：2016
- 出版时间：February 19, 2016
- 年：2016
- 卷：18
- 期：4
- 页码：676-679
- 全文大小：405K
- ISSN：1523-7052
文摘
A new chemoselective iodocarbocyclization of allenyl arenes was developed leading to the formation of 2-iodoindenes. In acetonitrile or nitromethane, electrophilic sources of iodine cations react selectively with the C2–C3 double bond of 1-arylallenes to give, after anti nucleophilic attack of the aromatic ring, 2-iodoindene products in high yields. Variations of the allenic skeletons revealed the high 5-endo selectivity and some competitive pathways of cyclization. Postfunctionalization reactions of the carbon–iodine bond, via Pd- and Cu-cross-couplings, gave rise to substituted indenes in good to excellent yields.