28856-77-1Relevant articles and documents
RADICAL NUCLEOPHILIC SUBSTITUTION OF INACTIVATED HETEROARYL BROMIDES
Yakubov, A. P.,Belen'kii, L. I.,Gol'dfarb, Ya. L.
, p. 2344 - 2347 (1981)
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Nucleophilic C-H Etherification of Heteroarenes Enabled by Base-Catalyzed Halogen Transfer
Bandar, Jeffrey S.,Klaus, Danielle R.,Puleo, Thomas R.
supporting information, p. 12480 - 12486 (2021/08/24)
We report a general protocol for the direct C-H etherification of N-heteroarenes. Potassium tert-butoxide catalyzes halogen transfer from 2-halothiophenes to N-heteroarenes to form N-heteroaryl halide intermediates that undergo tandem base-promoted alcohol substitution. Thus, the simple inclusion of inexpensive 2-halothiophenes enables regioselective oxidative coupling of alcohols with 1,3-azoles, pyridines, diazines, and polyazines under basic reaction conditions.
General Method for the Asymmetric Synthesis of N-H Sulfoximines via C-S Bond Formation
Argent, Stephen P.,Lewis, William,Mendon?a Matos, Priscilla,Moore, Jonathan c.,Stockman, Robert A.
supporting information, (2020/03/30)
A versatile method for the synthesis of enantioenriched N-H sulfoximines is reported. The approach stems from the organomagnesium-mediated ring opening of novel cyclic sulfonimidate templates. The reactions proceed in high yield and with excellent stereofidelity with alkyl, aryl, and heteroaryl Grignard reagents. The chiral auxiliary is readily removed from the resultant sulfoximines via an unusual oxidative debenzylation protocol that utilizes molecular oxygen as the terminal oxidant. This provides a general strategy for the synthesis of highly enantioenriched N-H sulfoximines.
