Methylene chloride, coupling reagent

Methylene chloride also acts as a coupling reagent but is less effective than methylene bromide. Examples of coupling material containing structure are shown in Table II. 

Thieno benzazepine 109 was synthesized in moderate yield by oxidative biaryl-coupling using the hypervalent iodine reagent phenyliodine(lll)bis (trifluoroacetate) (FIFA) and BF3 OEt2 as the activating agent in methylene chloride (Equation (16) (2002X8581)). 

Solvated perfluoroalkyl zinc reagents have been prepared by reaction of perfluoroalkyl iodides with zinc in ethereal solvents such as dioxane [36,37]. Self-coupled and cross-coupled products can be formed when a mixture of acetic anhydride and methylene chloride was used [38-40] (Scheme 11). 

Oxidative phenol coupling. Schwartz et al. report that TTFA is an effective reagent for intramolecular oxidative phenol coupling. Thus oxidation of the diaryl-propane derivative (I) with 1 molar eq. of n i A in methylene chloride affords the... 

Homoallyl bromide 314, prepared from readily available non-racemic ester 313, was converted to the Grignard reagent, which reacted with non-racemic epoxide, derived from D-maUc acid, to afford the alcohol 305. Ozonolysis of the alkene gave a ketone, which was converted into enol tri-flate 316. Ni-catalyzed cross coupling with trimethylsilylmethyl magnesium chloride afforded the allyl silane, which was converted into the allyl stan-nane 317. The asymmetric allylation of 313 with 317 provided 304 with a ration of 8.5 1. Methyl etherification and oxidative cleavage of exo-methylene... 

---