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Volumn 46, Issue 46, 2007, Pages 8790-8795

Ni-catalyzed cascade formation of C(sp3)-C(sp3) bonds by cyclization and cross-coupling reactions of iodoalkanes with alkyl zinc halides

Author keywords

C C coupling; Density functional calculations; Homogeneous catalysis; Nickel; Radical reactions

Indexed keywords

CATALYST ACTIVITY; CHEMICAL BONDS; CYCLIZATION; DENSITY FUNCTIONAL THEORY; LIGANDS; ZINC COMPOUNDS;

EID: 36749022699     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200702528     Document Type: Article
Times cited : (253)

References (54)
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    • The presence of heteroatoms in the substrate is not necessary for the reaction to take place. Thus, we have performed the cross-coupling reaction of 1-iodo-3-phenylpropane with 3-pentylzinc bromide under the standard conditions, which afforded the expected product in approximately 60% yield. Moreover, the reaction of 1-(but-3-enyl)-2-iodocyclopentane with the same organozinc compound gave the corresponding cyclization/cross-coupling derivative in about 70, yield. Again in these cases, these low polarity compounds could not be separated from by-products by column chromatography. Experimental details can be found in the Supporting Information
    • The presence of heteroatoms in the substrate is not necessary for the reaction to take place. Thus, we have performed the cross-coupling reaction of 1-iodo-3-phenylpropane with 3-pentylzinc bromide under the standard conditions, which afforded the expected product in approximately 60% yield. Moreover, the reaction of 1-(but-3-enyl)-2-iodocyclopentane with the same organozinc compound gave the corresponding cyclization/cross-coupling derivative in about 70 % yield. Again in these cases, these low polarity compounds could not be separated from by-products by column chromatography. Experimental details can be found in the Supporting Information.
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    • This association complex has been obtained by optimization after partial intrinsic reaction coordinate (IRC) calculation 15 cycles with the default Gaussian03 IRC parameters
    • This association complex has been obtained by optimization after partial intrinsic reaction coordinate (IRC) calculation (15 cycles with the default Gaussian03 IRC parameters).


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