Radical aminomethylation of unactivated alkenes

Béatrice Quiclet-Sire; Samir Z. Zard

doi:10.1021/ol801162m

Radical aminomethylation of unactivated alkenes

Béatrice Quiclet-Sire
, Samir Z. Zard

Laboratoire de Synthèse Organique

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

59 Citations (Scopus)

Abstract

(Chemical Equation Presented) S-Succinimidomethyl- and S-phthalimidomethyl xanthates are added efficiently to various alkenes resulting in an overall aminomethylation process. In contrast, under similar conditions, S-pyrrolidonyl xanthate gives rise mostly to oligomers. This unexpected difference in reactivity is attributed to the more important allylic character of the intermediate radical in the case of the imide derivative as compared to the lactam.

Original language	English
Pages (from-to)	3279-3282
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	15
DOIs	https://doi.org/10.1021/ol801162m
Publication status	Published - 1 Dec 2008
Externally published	Yes

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title = "Radical aminomethylation of unactivated alkenes",

abstract = "(Chemical Equation Presented) S-Succinimidomethyl- and S-phthalimidomethyl xanthates are added efficiently to various alkenes resulting in an overall aminomethylation process. In contrast, under similar conditions, S-pyrrolidonyl xanthate gives rise mostly to oligomers. This unexpected difference in reactivity is attributed to the more important allylic character of the intermediate radical in the case of the imide derivative as compared to the lactam.",

author = "B{\'e}atrice Quiclet-Sire and Zard, \{Samir Z.\}",

year = "2008",

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day = "1",

doi = "10.1021/ol801162m",

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T1 - Radical aminomethylation of unactivated alkenes

AU - Quiclet-Sire, Béatrice

AU - Zard, Samir Z.

PY - 2008/12/1

Y1 - 2008/12/1

N2 - (Chemical Equation Presented) S-Succinimidomethyl- and S-phthalimidomethyl xanthates are added efficiently to various alkenes resulting in an overall aminomethylation process. In contrast, under similar conditions, S-pyrrolidonyl xanthate gives rise mostly to oligomers. This unexpected difference in reactivity is attributed to the more important allylic character of the intermediate radical in the case of the imide derivative as compared to the lactam.

AB - (Chemical Equation Presented) S-Succinimidomethyl- and S-phthalimidomethyl xanthates are added efficiently to various alkenes resulting in an overall aminomethylation process. In contrast, under similar conditions, S-pyrrolidonyl xanthate gives rise mostly to oligomers. This unexpected difference in reactivity is attributed to the more important allylic character of the intermediate radical in the case of the imide derivative as compared to the lactam.

U2 - 10.1021/ol801162m

DO - 10.1021/ol801162m

M3 - Article

AN - SCOPUS:59949101791

SN - 1523-7060

VL - 10

SP - 3279

EP - 3282

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Radical aminomethylation of unactivated alkenes

Abstract

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