Alkynes as activators in the nickel-catalysed addition of organoboronates to aldehydes

G Takahashi, E Shirakawa, T Tsuchimoto…

Index: Takahashi, Go; Shirakawa, Eiji; Tsuchimoto, Teruhisa; Kawakami, Yusuke Chemical Communications, 2005 , # 11 p. 1459 - 1461

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Citation Number: 21

Abstract

The Ni(cod) 2 –4-octyne catalyst was found to be applicable to various combinations of organoboronates and aldehydes (Table 2). p-Tolylboronate 1a added to both electron-rich and -poor aromatic aldehydes (entries 1 and 2). Benzaldehyde (2a) accepted the addition of phenylboronates having a methoxy, trifluoromethyl, acetyl or hydroxymethyl group (entries 3–6). In contrast to more nucleophilic arylmetals such as arylmagnesium halides and aryllithiums, organoboronates are ...

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