Copper-catalyzed Ritter-type reaction of unactivated alkenes with dichloramine-T

Takumi Abe; Hiroyuki Takeda; Yoshihisa Miwa; Koji Yamada; Reiko Yanada; Minoru Ishikura

doi:10.1002/hlca.200900214

Copper-catalyzed Ritter-type reaction of unactivated alkenes with dichloramine-T

Takumi Abe, Hiroyuki Takeda, Yoshihisa Miwa, Koji Yamada, Reiko Yanada, Minoru Ishikura

Research output: Contribution to journal › Article › peer-review

27 Citations (Scopus)

Abstract

It was shown that dichloramine-T (1) reacted with cyclohexene in acetonitrile to give N¹-(2-chlorocyclohexyl) amidine 2a and N-(2-chlorocyclohexyl)acetamide (3) via the competitive addition of acetonitrile and N-chloro-N-tosylamino anion to cyclohexenechloronium ion. This reaction can be catalyzed by Cu(OAc)₂ , primarily affording 2a. Furthermore, the resulting 2a can be cyclized to benzimidazol 14a in good yield by treating with KOH in dioxane.

Original language	English
Pages (from-to)	233-241
Number of pages	9
Journal	Helvetica Chimica Acta
Volume	93
Issue number	2
DOIs	https://doi.org/10.1002/hlca.200900214
Publication status	Published - Feb 2010
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Biochemistry
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1002/hlca.200900214

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title = "Copper-catalyzed Ritter-type reaction of unactivated alkenes with dichloramine-T",

abstract = "It was shown that dichloramine-T (1) reacted with cyclohexene in acetonitrile to give N1-(2-chlorocyclohexyl) amidine 2a and N-(2-chlorocyclohexyl)acetamide (3) via the competitive addition of acetonitrile and N-chloro-N-tosylamino anion to cyclohexenechloronium ion. This reaction can be catalyzed by Cu(OAc)2 , primarily affording 2a. Furthermore, the resulting 2a can be cyclized to benzimidazol 14a in good yield by treating with KOH in dioxane.",

author = "Takumi Abe and Hiroyuki Takeda and Yoshihisa Miwa and Koji Yamada and Reiko Yanada and Minoru Ishikura",

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T1 - Copper-catalyzed Ritter-type reaction of unactivated alkenes with dichloramine-T

AU - Abe, Takumi

AU - Takeda, Hiroyuki

AU - Miwa, Yoshihisa

AU - Yamada, Koji

AU - Yanada, Reiko

AU - Ishikura, Minoru

PY - 2010/2

Y1 - 2010/2

N2 - It was shown that dichloramine-T (1) reacted with cyclohexene in acetonitrile to give N1-(2-chlorocyclohexyl) amidine 2a and N-(2-chlorocyclohexyl)acetamide (3) via the competitive addition of acetonitrile and N-chloro-N-tosylamino anion to cyclohexenechloronium ion. This reaction can be catalyzed by Cu(OAc)2 , primarily affording 2a. Furthermore, the resulting 2a can be cyclized to benzimidazol 14a in good yield by treating with KOH in dioxane.

AB - It was shown that dichloramine-T (1) reacted with cyclohexene in acetonitrile to give N1-(2-chlorocyclohexyl) amidine 2a and N-(2-chlorocyclohexyl)acetamide (3) via the competitive addition of acetonitrile and N-chloro-N-tosylamino anion to cyclohexenechloronium ion. This reaction can be catalyzed by Cu(OAc)2 , primarily affording 2a. Furthermore, the resulting 2a can be cyclized to benzimidazol 14a in good yield by treating with KOH in dioxane.

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JF - Helvetica Chimica Acta

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Copper-catalyzed Ritter-type reaction of unactivated alkenes with dichloramine-T

Abstract

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