Mutualism in organic synthetic chemistry:Simultaneous heterodehydrocoupling of hydrostannane and reduction of quinoline
Here we report a one-pot strategy to simultaneously achieve both the heterodehydrocoupling of hydrostannane and reduction of quinoline by using B(C6F5)3 as catalyst under mild conditions.This method realizes the synthesis of heteroatom-tin complexes(NSn/OSn/PSn/SSn)by the same cat-alyst system.With the assistance of quinoline,the substrate scope was broadened and ESn yield was significantly enhanced.During the reaction,the generated heterodehydrocoupling intermediate[ESnH]+[HB(C6Fs)3]-would accelerate the quinoline reduction by transforming 1,4-N-stannyl-dihydroquinoline intermediate into N-stannyl-tetrahydroquinoline whereas 1,4-N-stannyl-dihydroquinoline could serve as hydrogen acceptor to facilitate the conversion of[ESnH]+[HB(C6Fs)3]-intermediate to produce ESn(E=N/O/P/S).The metathetical reaction of N-stannyl-tetrahydroquinoline and EH rapidly generates ESn and tetrahydroquinolines,thus mutu-ally promoting the above process.The reaction mechanism is proposed on the basis of control ex-periments,capture and synthesis of key intermediates and deuterium experiments.
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维普
