Catalytic cross-coupling of alkylzinc halides with α-chloroketones

Journal of the American Chemical Society

Volumn 126, Issue 33, 2004, Pages 10240-10241

  Malosh, Chrysa F ^a   Ready, Joseph M ^a  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; ALPHA CHLOROKETONE; CARBONYL DERIVATIVE; CHLORINE; COPPER; HALIDE; KETONE; MAGNESIUM; ORGANOMETALLIC COMPOUND; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CROSS COUPLING REACTION; ENANTIOMER; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 4143087067     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0467768     Document Type: Article

References (24)

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15. Reactions of lithium dialkyl cuprates with α-bromo ketones: (a) Posner, G. H.; Sterling, J. J.; Whitten, C. E.; Lentz, C. M.; Brunelle, D. J. J. Am. Chem. Soc. 1975, 97, 107-118 and references therein.
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17. Tertiary alkylzinc reagents and tertiary α-chloro ketones provide negligible yields of the cross-coupled products.
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20. Control experiments verified formation of the zinc alkoxide under the conditions of eq 1. At elevated temperatures, ring contraction to generate cyclopentyl isopropyl ketone predominates. See the Supporting Information for details.
21. The copper enolate could exist primarily in the η-1 O-bound, η-1 C-bound or η-3 oxallyl form. For a theoretical study, see: Rosi, M.; Sgamellotti, A.; Floriani, C. J. Mol. Stuct. (THEOCHEM) 1999, 459, 57-65.
22. Additional examples can be found in the Supporting Information.
23. The uncatalyzed reaction occurs with inversion of configuration. See the Supporting Information for details.
24. Yamanaka, M.; Kato, S.; Nakamura, E. J. Am. Chem. Soc. 2004, 126, 6287-6293 and references therein.