Palladium-Catalyzed Arylation of α,α-Disubstituted Arylmethanols via Cleavage of a C−C or a C−H Bond To Give Biaryls
The palladium-catalyzed arylation of α,α-disubstituted arylmethanols with aryl halides proceeds not only via C−H bond cleavage at the ortho-position, but also via cleavage of the sp2−sp3 C−C bond with the liberation of ketones (β-carbon elimination) to give the corresponding biaryls. Both reactions...
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| Veröffentlicht in: | Journal of organic chemistry 2003-06, Vol.68 (13), p.5236-5243 |
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| container_end_page | 5243 |
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| container_issue | 13 |
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| container_title | Journal of organic chemistry |
| container_volume | 68 |
| creator | Terao, Yoshito Wakui, Hiroyuki Nomoto, Michiyo Satoh, Tetsuya Miura, Masahiro Nomura, Masakatsu |
| description | The palladium-catalyzed arylation of α,α-disubstituted arylmethanols with aryl halides proceeds not only via C−H bond cleavage at the ortho-position, but also via cleavage of the sp2−sp3 C−C bond with the liberation of ketones (β-carbon elimination) to give the corresponding biaryls. Both reactions appear to occur through common arylpalladium(II) alcoholate intermediates. The results of systematic studies with respect to which C−C or C−H bond is preferentially cleaved in the arylation are reported. Among the important findings is the selective elimination of ortho-substituted aryl groups even from aryl(diphenyl)methanols due to steric reasons. Thus, various biaryls having ortho-substituents can be produced efficiently by treatment of the corresponding aryl(diphenyl or dimethyl)methanols with aryl bromides and chlorides. |
| doi_str_mv | 10.1021/jo0344034 |
| format | Article |
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Both reactions appear to occur through common arylpalladium(II) alcoholate intermediates. The results of systematic studies with respect to which C−C or C−H bond is preferentially cleaved in the arylation are reported. Among the important findings is the selective elimination of ortho-substituted aryl groups even from aryl(diphenyl)methanols due to steric reasons. 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Org. Chem</addtitle><description>The palladium-catalyzed arylation of α,α-disubstituted arylmethanols with aryl halides proceeds not only via C−H bond cleavage at the ortho-position, but also via cleavage of the sp2−sp3 C−C bond with the liberation of ketones (β-carbon elimination) to give the corresponding biaryls. Both reactions appear to occur through common arylpalladium(II) alcoholate intermediates. The results of systematic studies with respect to which C−C or C−H bond is preferentially cleaved in the arylation are reported. Among the important findings is the selective elimination of ortho-substituted aryl groups even from aryl(diphenyl)methanols due to steric reasons. 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Org. Chem</addtitle><date>2003-06-27</date><risdate>2003</risdate><volume>68</volume><issue>13</issue><spage>5236</spage><epage>5243</epage><pages>5236-5243</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The palladium-catalyzed arylation of α,α-disubstituted arylmethanols with aryl halides proceeds not only via C−H bond cleavage at the ortho-position, but also via cleavage of the sp2−sp3 C−C bond with the liberation of ketones (β-carbon elimination) to give the corresponding biaryls. Both reactions appear to occur through common arylpalladium(II) alcoholate intermediates. The results of systematic studies with respect to which C−C or C−H bond is preferentially cleaved in the arylation are reported. Among the important findings is the selective elimination of ortho-substituted aryl groups even from aryl(diphenyl)methanols due to steric reasons. Thus, various biaryls having ortho-substituents can be produced efficiently by treatment of the corresponding aryl(diphenyl or dimethyl)methanols with aryl bromides and chlorides.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>12816483</pmid><doi>10.1021/jo0344034</doi><tpages>8</tpages></addata></record> |
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| source | ACS Publications |
| subjects | Chemistry Exact sciences and technology Noncondensed benzenic compounds Organic chemistry Preparations and properties |
| title | Palladium-Catalyzed Arylation of α,α-Disubstituted Arylmethanols via Cleavage of a C−C or a C−H Bond To Give Biaryls |
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