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Volumn 126, Issue 49, 2004, Pages 15964-15965

A unique catalyst effects the rapid room-temperature cross-coupling of organozinc reagents with carboxylic acid fluorides, chlorides, anhydrides, and thioesters

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; CHLORINE DERIVATIVE; FLUORIDE; KETONE DERIVATIVE; NICKEL COMPLEX; SILANE DERIVATIVE; STYRENE DERIVATIVE; THIOESTER; ZINC DERIVATIVE;

EID: 10344232706     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja044113k     Document Type: Article
Times cited : (197)

References (51)
  • 5
    • 10344259074 scopus 로고    scopus 로고
    • note
    • (b) For a review on ketone synthesis from acid chlorides, see ref 1a.
  • 35
    • 10344261468 scopus 로고    scopus 로고
    • note
    • We have found that Pd complexes are also capable of cross-coupling acid fluorides with organozinc halides and organoboronic acids.
  • 36
    • 10344231950 scopus 로고    scopus 로고
    • note
    • 2, and DMA only afforded the coupling product in 26, 33, and 49% yields, respectively.
  • 38
    • 10344233135 scopus 로고    scopus 로고
    • note
    • To ensure that the reaction proceeded to completion, the reaction mixture was stirred for 10 min before the reaction was quenched with 1 M HCl.
  • 39
    • 10344247621 scopus 로고    scopus 로고
    • In press
    • (a) Detailed investigation of the influence of styrene in anhydride cross-coupling will be reported. Bercot. E. A.; Rovis T. J. Am. Chem. Soc. In press.
    • J. Am. Chem. Soc.
    • Bercot, E.A.1    Rovis, T.2
  • 42
    • 10344226147 scopus 로고    scopus 로고
    • note
    • See Supporting Information for details.
  • 43
    • 10344222088 scopus 로고    scopus 로고
    • note
    • It has been reported that aldehyde is observed in the palladium-catalyzed coupling reaction of acid chlorides and organozinc compounds. See ref 5b.
  • 44
    • 0028825601 scopus 로고
    • Yields in these reactions are much higher than that of Ni(0)-catalyzed coupling of acyl chloride and Grignard reagents: Malanga, C.; Aronica, L. A.; Lardicci, L. Tetrahedron Lett. 1995, 36, 9185.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 9185
    • Malanga, C.1    Aronica, L.A.2    Lardicci, L.3
  • 45
    • 0004219714 scopus 로고    scopus 로고
    • Organozinc Chemistry
    • Schlosser, M., Ed.; John Wiley & Sons, Ltd.
    • (a) Nakamura, E. Organozinc Chemistry. In Organometallics in Synthesis: A Manual: Schlosser, M., Ed.; John Wiley & Sons, Ltd.: 2002; p 602.
    • (2002) Organometallics in Synthesis: A Manual , pp. 602
    • Nakamura, E.1
  • 51
    • 10344237519 scopus 로고    scopus 로고
    • note
    • We observed a significant exotherm under these conditions, which likely accelerated the coupling reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.