Palladium reagents

See also page 362, Section 3 page 365, Section 6 page 365, Section 7 page 373, Section 9 and page 400, Section 25. 

R SnRj (R = alkyl), LiCl Et02C(CH2) ZnI (n = 2, 3) (R02CCH2CH2)2Zn ArZnX 

R = aryl, heterocyclic, benzylic, vinylic X = halogen, inflate 

Organic Synthesis with Palladium Compounds, Springer, New York (1980) 

Palladium Reagents in Organic Syntheses, Academic Press, New York (1985) 

Palladium Reagents and Catalysts Innovations in Organic Synthesis, J. Wiley and Sons, New York (1995) 

Organic Synthesis with Palladium Compounds, Springer Verlag, New York (1980) Comprehensive Organometallic Chemistry, Pergamon (1982), Vol 8, Chpt 57 Angew Int 24 283 (1985) 

JOC 45 5223 (1980) (also 3-halo-2-aIken-4-olide) See also page 392, Section 22, for related reactions. 

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Other useful references are R. E. Heck, Palladium Reagents in Organic Synthesis Academic Press, New York, 1985, and J. Tsuji, Organic Synthesis with Palladium Compounds, Sptinger-Vedag, New York, 1980. 

TL2403). Thus, or /io-cyclopalladation of acetanilide 138 gave organo-palladium reagent 139. The or /io-vinylation of 139 afforded enone 140, which was then cyclized to quinoline 141 under acidic conditions. Notice this reaction requires stoichiometric amounts of Pd(OAc)2. 

A silica-supported palladium reagent has been used to convert iodobenzene to butyl benzoate, in the presence of CO and butanol. Diaryl ketones can also be... 

Tsuji J (1995) Palladium reagents and catalysts. Wiley, Chichester, p 19... 

J. Tsuji, Palladium Reagents and Catalysts New Perspectives for the 21st Century, Wiley-VCH, Weinheim, 2004. 

Heck, R.F., 1985, Palladium Reagents in Organic Synthesis , Academic Press, New York. Heumann, K., 1890, Ber. 23, 3431. 

Tsuji, J. Palladium Reagents and Catalysis John Wiley and Sons Chichester,... 

Each of the following reactions can be accomplished with a palladium reagent or catalyst. Write a detailed mechanism for each reaction. The number of equivalents of each reagent is given in parentheses. Specify the oxidation state of Pd in the intermediates. Be sure your mechanism accounts for the regeneration of catalytically active species in those reactions that are catalytic in palladium. 

Pyrimidinyl palladium reagents, prepared in situ from mercuric or iodo derivatives, react with 3,4-dihydro-2H-pyran to form isomeric products containing a dihydropyranyl group attached to C-5 of the substituted uracil... 

Several reports have been made of a successful catalyzed addition/ substitution reaction resulting in direct attachment of phosphorus to aromatic rings. The preparation of mixed triarylphosphines has been accomplished by the reaction of tin- or silicon-substituted diphe-nylphosphines with aryl halides catalyzed by palladium reagents.74 A similar transformation has also been reported using nickel catalysis.75 The addition/substitution of diphenylphosphine to triflate functionalized phenolic linkages has been of use for the preparation of substances as analogues of tyrosine-related amino acid derivatives, accomplished with catalysis by palladium acetate (Equation 4.29).76... 

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