Selective monomethylation of anilines by Cu(OAc)2-promoted cross-coupling with MeB(OH)2

Israel González; Jesús Mosquera; César Guerrero; Ramón Rodríguez; Jacobo Cruces

doi:10.1021/ol802882k

Selective monomethylation of anilines by Cu(OAc)₂-promoted cross-coupling with MeB(OH)₂

Israel González, Jesús Mosquera, César Guerrero, Ramón Rodríguez, Jacobo Cruces^*

^*Corresponding author for this work

Pure And Applied Chemistry

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

62 Citations (Scopus)

Abstract

N-Methylanilines are readily synthesized in high yields through the copper(ll)-promoted coupling of anilines and methylboronic acid. This method represents a new approach for the selective monomethylation of anilines, and it is the first reported example of a Chan-Lam coupling involving the use of methylboronic acid. An incubation period of the substrate with the copper reagent is needed before addition of the methylboronic acid.

Original language	English
Pages (from-to)	1677-1680
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	8
Early online date	20 Mar 2009
DOIs	https://doi.org/10.1021/ol802882k
Publication status	Published - 16 Apr 2009

Keywords

N-Methylanilines
anilines
Chan-Lam coupling

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10.1021/ol802882k

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title = "Selective monomethylation of anilines by Cu(OAc)2-promoted cross-coupling with MeB(OH)2",

abstract = "N-Methylanilines are readily synthesized in high yields through the copper(ll)-promoted coupling of anilines and methylboronic acid. This method represents a new approach for the selective monomethylation of anilines, and it is the first reported example of a Chan-Lam coupling involving the use of methylboronic acid. An incubation period of the substrate with the copper reagent is needed before addition of the methylboronic acid.",

keywords = "N-Methylanilines, anilines, Chan-Lam coupling",

author = "Israel Gonz{\'a}lez and Jes{\'u}s Mosquera and C{\'e}sar Guerrero and Ram{\'o}n Rodr{\'i}guez and Jacobo Cruces",

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T1 - Selective monomethylation of anilines by Cu(OAc)2-promoted cross-coupling with MeB(OH)2

AU - González, Israel

AU - Mosquera, Jesús

AU - Guerrero, César

AU - Rodríguez, Ramón

AU - Cruces, Jacobo

PY - 2009/4/16

Y1 - 2009/4/16

N2 - N-Methylanilines are readily synthesized in high yields through the copper(ll)-promoted coupling of anilines and methylboronic acid. This method represents a new approach for the selective monomethylation of anilines, and it is the first reported example of a Chan-Lam coupling involving the use of methylboronic acid. An incubation period of the substrate with the copper reagent is needed before addition of the methylboronic acid.

AB - N-Methylanilines are readily synthesized in high yields through the copper(ll)-promoted coupling of anilines and methylboronic acid. This method represents a new approach for the selective monomethylation of anilines, and it is the first reported example of a Chan-Lam coupling involving the use of methylboronic acid. An incubation period of the substrate with the copper reagent is needed before addition of the methylboronic acid.

KW - N-Methylanilines

KW - anilines

KW - Chan-Lam coupling

UR - http://www.scopus.com/inward/record.url?scp=65249102909&partnerID=8YFLogxK

U2 - 10.1021/ol802882k

DO - 10.1021/ol802882k

M3 - Article

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SP - 1677

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JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

Selective monomethylation of anilines by Cu(OAc)₂-promoted cross-coupling with MeB(OH)₂

Abstract

Keywords

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