Regio- and Chemoselective Direct Generation of Functionalized Aromatic Aluminum Compounds Using Aluminum Ate Base

Regio- and Chemoselective Direct Generation of Functionalized Aromatic Aluminum Compounds Using Aluminum Ate Base

A regio- and chemoselective direct method for generation of functionalized aromatic aluminum compounds through deprotonative directed ortho-alumination using triisobutyl(tetramethylpiperidino)aluminate ( i Bu3Al(TMP)Li), prepared by mixing of triisobutylaluminum ( i Bu3Al) and lithium tetramethylpip...

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Veröffentlicht in:Journal of the American Chemical Society 2004-09, Vol.126 (34), p.10526-10527
Hauptverfasser: Uchiyama, Masanobu, Naka, Hiroshi, Matsumoto, Yotaro, Ohwada, Tomohiko
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Chemistry
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Reactivity and mechanisms
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container_end_page 10527
container_issue 34
container_start_page 10526
container_title Journal of the American Chemical Society
container_volume 126
creator Uchiyama, Masanobu
Naka, Hiroshi
Matsumoto, Yotaro
Ohwada, Tomohiko
description A regio- and chemoselective direct method for generation of functionalized aromatic aluminum compounds through deprotonative directed ortho-alumination using triisobutyl(tetramethylpiperidino)aluminate ( i Bu3Al(TMP)Li), prepared by mixing of triisobutylaluminum ( i Bu3Al) and lithium tetramethylpiperidide (LTMP) in THF, has been developed. Deprotonative alumination of various functionalized benzenes with the use of i Bu3Al(TMP)Li proved effective for the direct generation of various ortho-functionalized aluminum aromatic and heteroaromatic derivatives, particularly those with electrophilic functional groups such as cyano, amide, and halogen. Direct alumination, followed by electrophilic trapping (with I2), provided a convenient preparative method for 1,2- or 1,2,3-multisubstituted aromatic compounds. The functionalized aromatic aluminate intermediate also was found to undergo copper- and palladium-catalyzed C−C bond-forming reactions very efficiently and highly regio- and chemoselectively.
doi_str_mv 10.1021/ja0473236
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Am. Chem. Soc</addtitle><date>2004-09-01</date><risdate>2004</risdate><volume>126</volume><issue>34</issue><spage>10526</spage><epage>10527</epage><pages>10526-10527</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><coden>JACSAT</coden><abstract>A regio- and chemoselective direct method for generation of functionalized aromatic aluminum compounds through deprotonative directed ortho-alumination using triisobutyl(tetramethylpiperidino)aluminate ( i Bu3Al(TMP)Li), prepared by mixing of triisobutylaluminum ( i Bu3Al) and lithium tetramethylpiperidide (LTMP) in THF, has been developed. Deprotonative alumination of various functionalized benzenes with the use of i Bu3Al(TMP)Li proved effective for the direct generation of various ortho-functionalized aluminum aromatic and heteroaromatic derivatives, particularly those with electrophilic functional groups such as cyano, amide, and halogen. Direct alumination, followed by electrophilic trapping (with I2), provided a convenient preparative method for 1,2- or 1,2,3-multisubstituted aromatic compounds. The functionalized aromatic aluminate intermediate also was found to undergo copper- and palladium-catalyzed C−C bond-forming reactions very efficiently and highly regio- and chemoselectively.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>15327295</pmid><doi>10.1021/ja0473236</doi><tpages>2</tpages></addata></record>
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subjects Chemistry
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Reactivity and mechanisms
title Regio- and Chemoselective Direct Generation of Functionalized Aromatic Aluminum Compounds Using Aluminum Ate Base
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