Allyl halides, reactions with

Table S.8. Cu(l)-catalyzed coupling reactions with allyl halides, a j 10mol%Cu(l) p...

These copper reagents do not react with epoxides, but they undergo SN2 reactions with allylic halides (equation II). These reagents also couple with acyl... 

NEOPENTYL IODIDE, 51, 44 Nerol, 54, 70 Neryl chloride, 54, 70 Nickel carbonyl, precautions for handling, 52, 117 reaction with allyl halides,... 

The phase-transfer catalysed reaction of nickel tetracarbonyl with sodium hydroxide under carbon monoxide produces the nickel carbonyl dianions, Ni,(CO) 2- and Ni6(CO)162, which convert allyl chloride into a mixture of but-3-enoic and but-2-enoic acids [18]. However, in view of the high toxicity of the volatile nickel tetracarbonyl, the use of the nickel cyanide as a precursor for the carbonyl complexes is preferred. Pretreatment of the cyanide with carbon monoxide under basic conditions is thought to produce the tricarbonylnickel cyanide anion [19], as the active metal catalyst. Reaction with allyl halides, in a manner analogous to that outlined for the preparation of the arylacetic acids, produces the butenoic acids (Table 8.7). 

Scheme 57 illustrates an example of this process coupling of the lithio reagent derived from vinyl stannane 237 with epoxide 242 leads to the C-disaccharide derivative 243 in good yield. A double transmetallation to give an organocopper reagent 244 can facilitate the C-glycosylation reaction with allyl halides [80] (Scheme 58). 

Michael addition reactions, 4, 302 reactions with allyl halides, 4, 301 Pyrrole-2-carboxylic acid, 1-methyl-conformation, 4, 194 esters... 

Acemoglu L, Williams JMJ (2002) Synthetic Scope of the Tsuji-Trost Reaction with Allylic Halides, Carboxylates, Ethers, and Related Oxygen Nucleophiles as Starting Compounds. In Negishi E, de Meijere A (eds) Handbook of Organopalladium Chemistry for Organic Synthesis. Wiley, New York, p 1689... 

In the corresponding reaction with allylic halides, -alkylated products were formed by direct C-alkylation as well as by N-alkylation followed by N - C [3,3]sigmatropic... 

Formation from the metal 5.8.2.12.1 Reaction with Ph3SiLi 5.8.3.4.2 Reaction with RNC 5.8.2.15.1 Reaction with allyl halides S.8.2.9.4 Reaction with disilacyclobutene ... 

Reaction with Ph3SiH 5.S.3.2.3 Reaction with BrCHjCHjBR 5.S.2.9.2 Reaction with C5F5N 5.S.2.9.2 Reaction with R3GeX 5.8.4.3.1 Reaction with R3PbCl, RjPbClj.- 5.8.6.2 Reaction with (CF3C0>20 5.S.2.9.2 Reaction with acyl halides 5.8.2.9.2 Reaction with allyl halides 5.8.2.9.4 Reaction with silicon halides 5.8.3.3.1 CjMoNajO,... 

Reaction with allyl halides 5.8.19.4 Reaction with onium compounds ... 

Mo(CO)3(CH3CN)3 Reaction with tf-CpSnR3 5.S.5.6.4 Reaction with MejSnCjH, 5.8.2.11.1 Reaction with allyl halides 5.8.2.9.4 C.HjNOjRu... 

Tetrafluoropyridyl organometallic reagents can be prepared by reaction of 4-bromotetra-fluoro- or tctrafluoro-4-iodopyridine with zinc or cadmium in dimethylformamide at room temperature.83 Metathesis of these reagents with copper(l) bromide affords the (2.3,5,6-tetra-fluoro-4-pyridyl)copper reagent. The latter species undergoes high-yield substitution reactions with allyl halides, vinyl iodides, aryl iodides, and alkanoyl halides. 

---