Iron-Catalyzed Ring-Opening Azidation and Allylation of O‑Heterocycles

We have established the first catalytic C–C and C–N bond formation reactions of O-heterocycles (e.g., tetrahydrofuran, phthalane, and lactone derivatives) using iron trichloride as a catalyst in the presence of TMSN3 or allylsilanes accompanied by the ring opening of O-heterocycles. The reactions sm...

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Veröffentlicht in:	Organic letters 2013-10, Vol.15 (20), p.5282-5285
Hauptverfasser:	Sawama, Yoshinari, Shibata, Kyoshiro, Sawama, Yuka, Takubo, Masato, Monguchi, Yasunari, Krause, Norbert, Sajiki, Hironao
Format:	Artikel
Sprache:	eng
Schlagworte:	Alcohols - chemical synthesis Alcohols - chemistry Allyl Compounds - chemistry Azides - chemistry Carboxylic Acids - chemical synthesis Carboxylic Acids - chemistry Catalysis Chlorides - chemistry Ferric Compounds - chemistry Heterocyclic Compounds - chemistry Molecular Structure
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container_issue	20
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container_title	Organic letters
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creator	Sawama, Yoshinari Shibata, Kyoshiro Sawama, Yuka Takubo, Masato Monguchi, Yasunari Krause, Norbert Sajiki, Hironao
description	We have established the first catalytic C–C and C–N bond formation reactions of O-heterocycles (e.g., tetrahydrofuran, phthalane, and lactone derivatives) using iron trichloride as a catalyst in the presence of TMSN3 or allylsilanes accompanied by the ring opening of O-heterocycles. The reactions smoothly proceeded at room temperature to give the corresponding primary saturated alcohols from the 2-substituted tetrahydrofurans, ortho-substituted benzyl alcohols from phthalanes, and saturated carboxylic acids from lactones in high yields.
doi_str_mv	10.1021/ol402511r
format	Article
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Lett</addtitle><date>2013-10-18</date><risdate>2013</risdate><volume>15</volume><issue>20</issue><spage>5282</spage><epage>5285</epage><pages>5282-5285</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>We have established the first catalytic C–C and C–N bond formation reactions of O-heterocycles (e.g., tetrahydrofuran, phthalane, and lactone derivatives) using iron trichloride as a catalyst in the presence of TMSN3 or allylsilanes accompanied by the ring opening of O-heterocycles. The reactions smoothly proceeded at room temperature to give the corresponding primary saturated alcohols from the 2-substituted tetrahydrofurans, ortho-substituted benzyl alcohols from phthalanes, and saturated carboxylic acids from lactones in high yields.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>24083667</pmid><doi>10.1021/ol402511r</doi><tpages>4</tpages></addata></record>
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subjects	Alcohols - chemical synthesis Alcohols - chemistry Allyl Compounds - chemistry Azides - chemistry Carboxylic Acids - chemical synthesis Carboxylic Acids - chemistry Catalysis Chlorides - chemistry Ferric Compounds - chemistry Heterocyclic Compounds - chemistry Molecular Structure
title	Iron-Catalyzed Ring-Opening Azidation and Allylation of O‑Heterocycles
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