By Furstner A
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Extra resources for Active Metals
The use of the traditional organolithium or Grignard precursors can be circumvented by using a highly reactive zero-valent copper which undergoes direct oxidative addition to organic halides . Significantly, the organocopper reagents prepared in our laboratories with this form of active copper may incorporate a wide variety of functionalities, such as allyl, nitrile, chloride, fluoride, epoxidc, ketone, and ester moieties. These functionalized organocopper reagents undergo many of the same reactions as other organocopper species, including cross-coupling reactions with acid chlorides, 1,6conjugate additions with a$-unsaturated carbonyl compounds, and intermolecular and intramolccular epoxide-opening reactions.
3 Reactions of Organozinc Reagents with Acid Chlorides Once the organozinc reagent is formed, it easily transmetallates to copper under mild conditions, yielding a highly functionalized cuprate. For example, the organozinc reagent can be added to CuCN . LiBr at -35 "C giving RCu(CN)ZnCl. When reacted with various acid chlorides, this organocopper species gives highly functionalized asymmetrical ketones in high yields. Representative examples of this type of transformation are shown in Table 1-13.
2 Kieke Magnesium,Culcium. Strontium, und Bnrium W F H 3 13 4CH3CCCI -20 "c, It H3 El Scheme 1-7. Reaction of thc 1,2-bis(methylene)cyclohcxane-magnesiurn complex with an ester. Table 1-4. Reactions of magnesium complexes of 1,2-dimethylenecycloalkaneswith bis-electrophiles. Entry Dimea) Electrophile Yieldb) (96) Product Reaction conditionc) A la la Br(CH2)4Br la Br(CH2)dBr la la a 75(81) 81 (CH,),Br 75(87) 14 I Riekr Metals: Highly Rructive Metal Powders Table 1-4. (continued) Entry Dieilea) Electrophilc Product Yieldb)(a) Reaction condition'" 7 la -(78) F 8 la 415) B 9 la 440) B 10 la 52(67) €3 11 Ib 60(70) D 12 lc 73 C 13 Ic 77(86) D 14 Ic 46(59) R 15 la 89 B a) (1 a) 1,2-bis(methylene)cyclohexane; (1 b) 1,2-bis(methylene)cycIopentane; ( I c) I ,2-bis(methylene)cycloheptane.
Active Metals by Furstner A