Copper catalyzed oxidation of organozinc halides

Su, Xueying; Fox, David J.; Blackwell, David T.; Tanaka, Kiyotaka; Spring, David R.

doi:10.1039/b610218b

Cited by 27 publications

(16 citation statements)

References 37 publications

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“…Notably, the coupling proceeded to provide predominately a “head-to-tail” coupling rather than either of the two possible symmetrical coupling products (Scheme 167). 316 …”

Section: Reaction Of Carbanions and Carbanion Equivalentsmentioning

confidence: 99%

Aerobic Copper-Catalyzed Organic Reactions

et al. 2013

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24 peroxide [Cu I (pyr)(tpb)] 10 mol % TBHP, 1 atm O 2 , 1:2 AcOH/pyr, rt, 24 h ∼2.5 26 74 g 35 25 n-hexane aldehyde CuCl 2 , 18-crown-6 1 atm O 2 , MeCHO, CH 2 Cl 2 , 70 °C, 24 h 2.4 91 h 9 34a 26 n-decane aldehyde Cu II Cl 16 Pc-AM(PS) 3 equiv of PhCHO, MeCN, 1 atm O 2 , 50 °C 15.4 100 i 61 a See Chart 2 for ligand structures. b Also 28% cyclohexene. c Also 26% cyclohexene. d Mixture of alcohol and hydroperoxide. e Remainder of product is cyclohexene. f Approximately 93:7 of 1-adamantol/2-adamantol. g Approximately 98:2 of 1-adamantol/2-adamantol. h Afforded oxidation products in an approximately 1:1 ratio at the 2-and 3-positions. i Mixture of decanones.

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“…Notably, the coupling proceeded to provide predominately a “head-to-tail” coupling rather than either of the two possible symmetrical coupling products (Scheme 167). 316 …”

Section: Reaction Of Carbanions and Carbanion Equivalentsmentioning

confidence: 99%

Aerobic Copper-Catalyzed Organic Reactions

et al. 2013

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“…[1][2][3][4] Lipshutz et al [1] and, more recently, Knochel et al [2] showed that, at low temperature, oxidation of mixed organocuprates RR'CuLi gives the heterocoupling product RÀR' in good yield. [1][2][3][4] Lipshutz et al [1] and, more recently, Knochel et al [2] showed that, at low temperature, oxidation of mixed organocuprates RR'CuLi gives the heterocoupling product RÀR' in good yield.…”

Section: Gørard Cahiez* Christophe Duplais and Julien Buendiamentioning

confidence: 99%

Manganese‐Catalyzed Oxidative Cross‐Coupling of Grignard Reagents with Oxygen as an Oxidant

2009

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“…Until now, only rare examples of oxidative cross-coupling reactions have been described. [1][2][3][4] Lipshutz et al [1] and, more recently, Knochel et al [2] showed that, at low temperature, oxidation of mixed organocuprates RR'CuLi gives the heterocoupling product RÀR' in good yield. Both reactions use a stoichiometric amount of copper.…”

Section: Gørard Cahiez* Christophe Duplais and Julien Buendiamentioning

confidence: 99%