4.8 Article

Use of the 2-Pyridinesulfonyloxy Leaving Group for the Fast Copper-Catalyzed Coupling Reaction at Secondary Alkyl Carbons with Grignard Reagents

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ORGANIC LETTERS
卷 21, 期 9, 页码 3247-3251

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AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b00976

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  1. KAKENHI [26410111]
  2. Grants-in-Aid for Scientific Research [26410111] Funding Source: KAKEN

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Investigation of the copper-catalyzed coupling reaction of 2-pyridinesulfonates with Grignard reagents revealed that reactions with catalytic Cu(OTf)(2) were completed in <40 min. The results differed from those of the previous CuI-catalyzed reactions of tosylates in the presence of additives (LiOMe and TMEDA) for 12-24 h. It was shown that the preferred coordination of the leaving group to the reagents accelerated the reaction. Successful reagents were MeMgCl and other RMgX. Complete inversion was established.

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