Heteroaromatic Tosylates in the Regioselective Heck Reaction

Next, tosylated hydroxypyrimidines were tested in the regioselective Heck reaction using NVA and n-butyl vinyl ether in order to investigate the influence of the heteroaromatic core system on the catalytic outcome (Scheme 5.3). Similar yields of the vinylated pyrimidines compared to the pyridine equivalents were achieved indicating a robust catalytic system. Even a double Heck reaction could be accomplished yielding 56 in 36 % corresponding to an average of 60 % yield of each vinylation. 

In the following, the regioselective Heck reaction of heteroaromatic tosylates and electron rich olefins will be presented and discussed. This protocol constitutes the first general strategy for the palladium catalyzed olefination of pyridyl tosylates obtaining perfect a-regioselectivity. 

In Chap. 5, a presentation of the related regioselective Heck reaction of heteroaromatic tosylates is given. The work was conducted in collaboration with Dr. Anders Thyboe Lindhardt, Dr. Mouloud Dekhane from AstraZeneca, and B.Sc. Julie Groulefif. 

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