Carbonylative coupling of organozinc reagents in the presence and absence of aryl iodides: Synthesis of unsymmetrical and symmetrical ketones

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 6, 1997, Pages 865-870

  Jackson, Richard F W ^a   Turner, Debra ^a   Block, Michael H ^b  

^a NEWCASTLE UNIVERSITY   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748645943     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a606394b     Document Type: Article

References (20)

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5. For a recent synthesis and references to earlier work, see F. G. Salituro and I. A. McDonald, J. Org. Chem., 1988, 53, 6138.
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8. For a preliminary communication on part of the work discussed in this paper, see: R. F. W. Jackson, D. Turner and M. H. Block, J. Chem. Soc. Chem. Commun., 1995, 2207.
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10. For an important preliminary report which describes the in situ carbonylative coupling of aryl iodides with alkyl iodides mediated by zinc and palladium(0), see Y. Tamaru, H. Ochiai, Y. Yamada and Z.-I. Yoshida, Tetrahedron Lett., 1983, 24, 3869.
11. These conditions are derived from those reported by Salituro and McDonald for an analogous deprotection (ref. 5 above).
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17. For a discussion of the mechanism of self-coupling of arylboronic acids to give biaryls under palladium catalysis, which also invokes oxidation by molecular oxygen, see M. Moreno-Mañas, M. Pérez and R. Pleixats. J. Org. Chem., 1996, 61, 2346 and references cited therein.
18. For related observations on the homocoupling of arylstannanes, see V. Farina, B. Krishnan, D. R. Marshall and G. P. Roth, J. Org. Chem., 1993, 58, 5434.
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