Direct Cyclization of Tertiary Aryl Amines with Iodonium Ylides
Zhiguo Zhao
School of Chemistry and Chemical Engineering, Key Laboratory of the Colloid and Interface Chemistry, Ministry of Education, Shandong University, 27 Shanda Nanlu, Jinan, 250100 Shandong, China
Search for more papers by this authorYongrui Luo
School of Chemistry and Chemical Engineering, Key Laboratory of the Colloid and Interface Chemistry, Ministry of Education, Shandong University, 27 Shanda Nanlu, Jinan, 250100 Shandong, China
Search for more papers by this authorDr. Shuya Liu
School of Chemistry and Chemical Engineering, Key Laboratory of the Colloid and Interface Chemistry, Ministry of Education, Shandong University, 27 Shanda Nanlu, Jinan, 250100 Shandong, China
Search for more papers by this authorLiang Zhang
School of Chemistry and Chemical Engineering, Key Laboratory of the Colloid and Interface Chemistry, Ministry of Education, Shandong University, 27 Shanda Nanlu, Jinan, 250100 Shandong, China
Search for more papers by this authorDr. Lei Feng
School of Chemistry and Chemical Engineering, Key Laboratory of the Colloid and Interface Chemistry, Ministry of Education, Shandong University, 27 Shanda Nanlu, Jinan, 250100 Shandong, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Yao Wang
School of Chemistry and Chemical Engineering, Key Laboratory of the Colloid and Interface Chemistry, Ministry of Education, Shandong University, 27 Shanda Nanlu, Jinan, 250100 Shandong, China
Search for more papers by this authorZhiguo Zhao
School of Chemistry and Chemical Engineering, Key Laboratory of the Colloid and Interface Chemistry, Ministry of Education, Shandong University, 27 Shanda Nanlu, Jinan, 250100 Shandong, China
Search for more papers by this authorYongrui Luo
School of Chemistry and Chemical Engineering, Key Laboratory of the Colloid and Interface Chemistry, Ministry of Education, Shandong University, 27 Shanda Nanlu, Jinan, 250100 Shandong, China
Search for more papers by this authorDr. Shuya Liu
School of Chemistry and Chemical Engineering, Key Laboratory of the Colloid and Interface Chemistry, Ministry of Education, Shandong University, 27 Shanda Nanlu, Jinan, 250100 Shandong, China
Search for more papers by this authorLiang Zhang
School of Chemistry and Chemical Engineering, Key Laboratory of the Colloid and Interface Chemistry, Ministry of Education, Shandong University, 27 Shanda Nanlu, Jinan, 250100 Shandong, China
Search for more papers by this authorDr. Lei Feng
School of Chemistry and Chemical Engineering, Key Laboratory of the Colloid and Interface Chemistry, Ministry of Education, Shandong University, 27 Shanda Nanlu, Jinan, 250100 Shandong, China
Search for more papers by this authorCorresponding Author
Prof. Dr. Yao Wang
School of Chemistry and Chemical Engineering, Key Laboratory of the Colloid and Interface Chemistry, Ministry of Education, Shandong University, 27 Shanda Nanlu, Jinan, 250100 Shandong, China
Search for more papers by this authorGraphical Abstract
In an impressive show of independence, iodonium ylides underwent direct cyclization with unmodified tertiary aryl amines (see scheme). The transformation, which was developed on the basis of the exceptional finding that iodonium ylides could cleave the C(sp3)−H bonds of tertiary aryl amines, proceeded in the absence of a transition-metal catalyst and without the use of an additional initiator/oxidant.
Abstract
Described herein is a direct cyclization of simple tertiary aryl amines with iodonium ylides leading to a broad range of N-heterocycles. Completely different from the known reactivity of iodonium ylides, the finding reported herein is that an iodonium ylide is capable of cleaving a C(sp3)−H bond and accepting two hydrogen atoms of a tertiary aryl amine, thus inducing a novel cyclization process. This transformation can proceed without the assistance of a transition-metal catalyst and eliminates the need for the premodification of the amine or the use of an additional initiator/oxidant.
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