In order to study the possibility of the extension of the phase transfer catalytic (PTC) arylation reactions to heterocyclic compounds, three pyridinediazonium tetrafluoroborates such as 2-chloro-3-pyridinediazonium tetrafluoroborate, 2-chloro-5-pyridinediazonium tetrafluorborate, and 3-pyridinediazonium tetrafluoroborate were investigated. PTC reactions of the 2-chloro-3-pyridinediazonium tetrafluoroborate and 2-chloro-5-pyridinediazonium tetrafluoroborate with potassium acetate in benzene produced the corresponding phenylpyridines in 56% and 17% yields, respectively. In similar PTC reactions of the diazonium salts with an additional aryne trapping reagent, furan, formatiom of [4+2] cycloaddition products along with phenylpyridines were noticed.

상이동 촉매 아릴화 반응의 해테로 방향족 화합물로의 확장 가능성 타진 연구로서 2-chloro-3-pyridinediazonium tetrafluoroborate, 2-chloro-5-pyridinediazoniumtetrafluoroborate, 그리고 3-pyridinediazonium tetrafluoroborate 등 3종의 피리딘 디아조늄 염의 상이동 촉매(phase transfer catalytic, PTC)반응을 조사하였다. 2-chloro-3-pyridinediazonium tetrafluoroborate, 2-chloro-5-pyridinediazonium tetrafluoroborate의 PTC 조건에서 초산칼륨과의 반응을 통한 아릴화는 벤젠 용매에서 수행된 두 반응에서 각각 56%, 17%의 피리딘 디아조늄 염을 얻었다. 첨가 아라인 포획 시약인 퓨란과 디아조늄염의 유사한 PTC 반응에서, 페닐피리딘과 함께 [4+2]사이클로 첨가 생성물의 생성이 확인되었다.