Reaction of an electrogenerated 'iminium cation pool' with organometallic reagents. Direct oxidative α-alkylation and -arylation of amine derivatives

Seiji Suga; Masayuki Okajima; Jun ichi Yoshida

doi:10.1016/S0040-4039(01)00128-9

Reaction of an electrogenerated 'iminium cation pool' with organometallic reagents. Direct oxidative α-alkylation and -arylation of amine derivatives

Seiji Suga, Masayuki Okajima, Jun ichi Yoshida

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

84 Citations (Scopus)

Abstract

We have developed an efficient direct oxidative α-alkylation and -arylation of carbamates based on the 'cation pool' method. Grignard reagents, organozinc compounds, and organoaluminum compounds are effective as carbon nucleophiles toward iminium cation pools generated by low temperature electrolysis of carbamates.

Original language	English
Pages (from-to)	2173-2176
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	11
DOIs	https://doi.org/10.1016/S0040-4039(01)00128-9
Publication status	Published - Mar 11 2001
Externally published	Yes

Keywords

Carbon-carbon bond formation
Cation pool
Electrochemical oxidation
Grignard reagents
Iminium cation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(01)00128-9

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title = "Reaction of an electrogenerated 'iminium cation pool' with organometallic reagents. Direct oxidative α-alkylation and -arylation of amine derivatives",

abstract = "We have developed an efficient direct oxidative α-alkylation and -arylation of carbamates based on the 'cation pool' method. Grignard reagents, organozinc compounds, and organoaluminum compounds are effective as carbon nucleophiles toward iminium cation pools generated by low temperature electrolysis of carbamates.",

keywords = "Carbon-carbon bond formation, Cation pool, Electrochemical oxidation, Grignard reagents, Iminium cation",

author = "Seiji Suga and Masayuki Okajima and Yoshida, {Jun ichi}",

note = "Funding Information: This research was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports, and Culture, Japan.",

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T1 - Reaction of an electrogenerated 'iminium cation pool' with organometallic reagents. Direct oxidative α-alkylation and -arylation of amine derivatives

AU - Suga, Seiji

AU - Okajima, Masayuki

AU - Yoshida, Jun ichi

N1 - Funding Information: This research was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports, and Culture, Japan.

PY - 2001/3/11

Y1 - 2001/3/11

N2 - We have developed an efficient direct oxidative α-alkylation and -arylation of carbamates based on the 'cation pool' method. Grignard reagents, organozinc compounds, and organoaluminum compounds are effective as carbon nucleophiles toward iminium cation pools generated by low temperature electrolysis of carbamates.

AB - We have developed an efficient direct oxidative α-alkylation and -arylation of carbamates based on the 'cation pool' method. Grignard reagents, organozinc compounds, and organoaluminum compounds are effective as carbon nucleophiles toward iminium cation pools generated by low temperature electrolysis of carbamates.

KW - Carbon-carbon bond formation

KW - Cation pool

KW - Electrochemical oxidation

KW - Grignard reagents

KW - Iminium cation

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U2 - 10.1016/S0040-4039(01)00128-9

DO - 10.1016/S0040-4039(01)00128-9

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SN - 0040-4039

VL - 42

SP - 2173

EP - 2176

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 11

ER -

Reaction of an electrogenerated 'iminium cation pool' with organometallic reagents. Direct oxidative α-alkylation and -arylation of amine derivatives

Abstract

Keywords

ASJC Scopus subject areas

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