In combination with CuI and an amine, catalyzes the Sonogashira coupling of terminal alkynes with aryl, vinyl, styryl and 2-pyridyl halides: Tetrahedron Lett., 4467 (1975). An improved procedure uses triethylamine in THF with catalytic amounts of CuI and the complex, avoiding the need for excess of the acetylene, and gives good yields under mild conditions, even with unreactive aryl bromides: J. Org. Chem., 63, 8551 (1998). For effect of high pressure in accelerating the reaction, see: Tetrahedron Lett., 36, 5547 (1995). For examples of the Stille coupling of arylstannanes with aryl triflates to give unsymmetrical biaryls, see: Org. Synth. Coll., 9, 553 (1998). For reviews, see: Adv. Met.-Org. Chem., 5, 1 (1996); Org. React, 50, 1 (1997). Catalyst for the carbonylation of benzyl halides with CO in an alcohol, in the presence of a base, e.g. 1,8-Bis(dimethyl-amino)-naphthalene, to give arylacetic esters: J. Org. Chem., 40, 532 (1975). Similarly, allylic chlorides are carbonylated to give predominantly ?-unsaturated acids at atmospheric pressure: Chem. Lett., 957 (1988), and bromo alkanols give lactones: J. Am. Chem. Soc., 102, 4193 (1980). Also catalyzes the low-pressure carbonylative cross-coupling of arylboronic acids with iodoarenes to give unsymmetrical biaryl ketones: Tetrahedron Lett., 34, 7595 (1993); J. Org. Chem., 63, 4726 (1998). Catalyzes the exclusively cis-addition of Tri-n-butyl-tin hydride,to alkynes at room temperature, to give vinylstannanes in good yield: J. Org. Chem., 55, 1857 (1990). In combination with acetic anhydride and triphenylphosphine, catalyzes the selective conversion of carboxylic acids to 1-alkenes of one less carbon atom: J. Org. Chem., 58, 29 (1993).
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