کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5280443 1385647 2008 4 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Ionic liquid-promoted one-pot oxidative Michael addition of TMSCN to Baylis-Hillman adducts
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Ionic liquid-promoted one-pot oxidative Michael addition of TMSCN to Baylis-Hillman adducts
چکیده انگلیسی

The first example of ionic liquid-promoted one-pot oxidative conjugate hydrocyanation of Baylis-Hillman adducts with trimethylsilyl cyanide (TMSCN) is reported. The oxidation of Baylis-Hillman adducts with IBX/[bmim]Br or isomerization-oxidation with NaNO3/[Hmim]HSO4 systems affords β-ketomethylene compounds or [E]-cinnamaldehydes, respectively. These α,β-unsaturated carbonyl compounds undergo Michael addition with TMSCN in the same vessel to afford the corresponding thermodynamically more stable β-cyanated products. Thermodynamically less stable 1,2-addition products were not formed. The present regioselective reactions are promoted by ionic liquids, which can be recycled easily for further use without any loss of efficiency.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron Letters - Volume 49, Issue 44, 27 October 2008, Pages 6360-6363
نویسندگان
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