Nickel-catalyzed β-boration of α,β-unsaturated esters and amides with bis(pinacolato)diboron

Organic Letters

Volumn 9, Issue 24, 2007, Pages 5031-5033

  Hirano, Koji ^a   Yorimitsu, Hideki ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANONE; AMIDE; BIS(PINACOLATO)DIBORON; BORON DERIVATIVE; BORONIC ACID DERIVATIVE; ESTER; NICKEL; ORGANOMETALLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

AMIDES; BORON COMPOUNDS; BORONIC ACIDS; BUTANONES; CATALYSIS; ESTERS; MOLECULAR STRUCTURE; NICKEL; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 36849015870     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702254g     Document Type: Article

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26. 3 gave the product in lower yields (ca. <20%).
27. A similar trend was observed in our previous work (see ref 8c and ref 12).
28. The fact that the substrates 1f and 1g bearing π-donor substituents on the benzene ring were more reactive than Ie is consistent with the existence and importance of the coordination (Table 2, entry 4 vs. entries 5 and 6). Namely, the more electron-rich carbonyl oxygen of nickelcoordinated If and Ig would have stronger interaction with bis(pinacolato)-diboron. The differences of reaction rates between amides and esters also support die assumption since the carbonyl oxygen of amides would be more electron-rich than that of esters (Table 2, entries 13-16).
29. 3SiOTf would proceed through a similar η-coordinated intermediate but not oxidative addition of the Si - Si bond of disilanes to the palladium complex, (a) Ogoshi, S.; Yoshida, T.; Nishida, T.; Morita, M.; Kurosawa, H. J. Am. Chem. Soc. 2001, 123, 1944-1950.
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32. 3-coordinated nickel complexes with the ketones formed by the action of the boronate was proposed as the key intermediate.
33. (c) Sieber, J. D.; Liu, S.; Morken, J. P. J. Am. Chem. Soc. 2007, 129, 2214-2215.
34. 2O resulted in 93% recovery of 2 (see eq 2). Nevertheless, in the catalytic reaction, we added cesium carbonate and methanol to the reaction mixture. These additives could change the reactivity of 2 or nickel complexes. equation persent