Chemoselective nitration of aromatic sulfonamides with tert-butyl nitrite.
نویسندگان
چکیده
A methodology for the efficient conversion of aromatic sulfonamides into their mono-nitro derivatives using tert-butyl nitrite is reported. The reaction exhibits a high degree of chemoselectivity for sulfonamide functionalized aryl systems, even in the presence of other sensitive or potentially reactive functionalities.
منابع مشابه
Convenient and mild synthesis of nitroarenes by metal-free nitration of arylboronic acids.
A novel methodology for the direct nitration of arylboronic acids has been developed. By using inexpensive tert-butyl nitrite various aromatic nitro compounds are produced in moderate to good yields (45-87%) without the need of any catalyst.
متن کاملDirect oxidative nitration of aromatic sulfonamides under mild conditions.
A direct nitration of aromatic sulfonamides using sodium nitrite as the nitrating agent has been developed. The reaction shows typically mono-substitution selectivity and can be enlarged to the gram scale with good yield.
متن کاملChemoselective N-tert-butoxycarbonylation and N-formylation of Amines by B(OSO3H)3/SiO2 as an Efficient Heterogeneous and Recyclable Catalyst
A simple, efficient, and cost-effective procedure for the N-tert-butoxycarbonylation and N-formylation of amines (primary, secondary) respectively, with di-tert-butyl dicarbonate and 85% aqueous formic acid under solvent-free condition using B(OSO3H)3/SiO2 (SBSA) as a heterogeneous and recyclable catalyst has been developed. We demonstrated that the resulting catalyst is applicable to various a...
متن کاملMetal-free nitrative cyclization of N-aryl imines with tert-butyl nitrite: dehydrogenative access to 3-nitroindoles.
We describe here a new metal-free route for the synthesis of 3-nitroindoles by the nitrative cyclization of N-aryl imines with tert-butyl nitrite. The radical transformation allows the assembly of the indole framework through oxidative cleavage of multi C-H bonds, a nitration, cyclization and isomerization cascade.
متن کاملCopper(II)-promoted direct conversion of methylarenes into aromatic oximes.
A simple and efficient catalytic system for direct conversion of methylarenes into aromatic oximes has been developed, with Cu(OAc)2 as catalyst, NHPI (N-Hydroxyphthalimide) as additive, TBN (tert-butyl nitrite) as both the nitrogen source and the oxidant. This process proceeds under mild conditions, tolerates a wide range of substrates, affording the targeted aromatic oximes in 63-86% yields.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 49 5 شماره
صفحات -
تاریخ انتشار 2013