Suzuki Cross-Couplings of Unactivated Secondary Alkyl Bromides and Iodides

Journal of the American Chemical Society

Volumn 126, Issue 5, 2004, Pages 1340-1341

  Zhou, Jianrong ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BATHOPHENANTHROLINE; BENZENEBORONIC ACID; BORON; BORONIC ACID DERIVATIVE; BROMIDE; BROMINE DERIVATIVE; CARBENE; CYCLOHEXANE; HALIDE; IODIDE; MAGNESIUM; NICKEL; PALLADIUM; PHENANTHROLINE DERIVATIVE; PHENYLCYCLOHEXANE; PHOSPHINE DERIVATIVE; SILICON; SULFONIC ACID DERIVATIVE; TIN; UNCLASSIFIED DRUG; VINYL DERIVATIVE; ZINC; ZIRCONIUM;

ARTICLE; CHEMICAL REACTION; CROSS COUPLING REACTION; HYDROGEN BOND; NEGISHI REACTION; SUZUKI REACTION;

ALKANES; BORONIC ACIDS; HYDROCARBONS, BROMINATED; HYDROCARBONS, IODINATED; NICKEL; ORGANOMETALLIC COMPOUNDS; PALLADIUM;

EID: 1042288193     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja039889k     Document Type: Article

References (34)

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32. The addition of water (1.0 equiv) leads to a 74% yield of phenylcyclohexane.
33. Notes: (a) For each entry, a single regio- and stereoisomer (> 50:1) is observed (see the Supporting Information). Our current hypothesis is that a radical intermediate may be involved. (b) Under our standard conditions, primary and tertiary alkyl bromides, alkylboronic acids, and ortho-substituted arylboronic acids are not suitable substrates.
34. Notes: (a) Under our standard conditions, alkyl chlorides and tertiary alkyl iodides are not suitable substrates. (b) Reactions of functionalized alkyl electrophiles proceed in lower yield.