Ligand-Controlled Copper(I)-Catalyzed Cross-Coupling of Secondary and Primary Alcohols to α‑Alkylated Ketones, Pyridines, and Quinolines
One hexanuclear Cu(I) cluster of 4,6-dimethylpyrimidine-2-thiolate efficiently catalyzes the dehydrogenative cross-coupling of secondary and primary alcohols to α-alkylated ketones with high selectivity. This transformation proceeds through a one-pot sequence of dehydrogenation of alcohols, condens...
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| Veröffentlicht in: | Organic letters 2018-02, Vol.20 (3), p.608-611 |
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| container_title | Organic letters |
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| creator | Tan, Da-Wei Li, Hong-Xi Zhu, Da-Liang Li, Hai-Yan Young, David James Yao, Jian-Lin Lang, Jian-Ping |
| description | One hexanuclear Cu(I) cluster of 4,6-dimethylpyrimidine-2-thiolate efficiently catalyzes the dehydrogenative cross-coupling of secondary and primary alcohols to α-alkylated ketones with high selectivity. This transformation proceeds through a one-pot sequence of dehydrogenation of alcohols, condensation of aldehydes and ketones, hydrogenation of the resulting α,β-unsaturated ketones, and dehydrogenation of the α-alkylated alcohols to generate α-alkylated ketones. This catalytic system also displays high activity for the annulation reaction of secondary alcohols with γ-amino- and 2-aminobenzyl alcohols to yield pyridines and quinolines, respectively. |
| doi_str_mv | 10.1021/acs.orglett.7b03726 |
| format | Article |
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Lett</addtitle><date>2018-02-02</date><risdate>2018</risdate><volume>20</volume><issue>3</issue><spage>608</spage><epage>611</epage><pages>608-611</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>One hexanuclear Cu(I) cluster of 4,6-dimethylpyrimidine-2-thiolate efficiently catalyzes the dehydrogenative cross-coupling of secondary and primary alcohols to α-alkylated ketones with high selectivity. This transformation proceeds through a one-pot sequence of dehydrogenation of alcohols, condensation of aldehydes and ketones, hydrogenation of the resulting α,β-unsaturated ketones, and dehydrogenation of the α-alkylated alcohols to generate α-alkylated ketones. 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| title | Ligand-Controlled Copper(I)-Catalyzed Cross-Coupling of Secondary and Primary Alcohols to α‑Alkylated Ketones, Pyridines, and Quinolines |
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