One-pot synthesis of secondary and tertiary amines from R(+)-limonene by tandem hydroformylation/reductive amination (hydroaminomethylation)

Cedric S. Graebin; Vera Lucia Eifler-Lima; Ricardo G. da Rosa

doi:10.1016/j.catcom.2007.10.008

One-pot synthesis of secondary and tertiary amines from R(+)-limonene by tandem hydroformylation/reductive amination (hydroaminomethylation)

Cedric S. Graebin
, Vera Lucia Eifler-Lima
, Ricardo G. da Rosa (Lead / Corresponding author)

Drug Discovery Unit

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

40 Citations (Scopus)

Abstract

In this work, we were able to synthesize, in good isolated yields, seven R(+)-limonene derived amines (five of that described for the first time) employing a rhodium catalysed hydroaminomethylation reaction. This protocol consists in an one-pot three step reaction: double bond hydroformylation, aldehyde/amine condensation and imine/enamine hydrogenation. Hydroaminomethylation, besides the high yields, has a high atom economy because just 1 mol of water is wasted per mol of limonene. Due to our catalytic optimizations, the reaction time was reduced from 48 h (described in the literature) to 10-24 h, as well as limonene isomerization was strongly minimized by the triphenylphosphine added.

Original language	English
Pages (from-to)	1066-1070
Number of pages	5
Journal	Catalysis Communications
Volume	9
Issue number	6
Early online date	16 Oct 2007
DOIs	https://doi.org/10.1016/j.catcom.2007.10.008
Publication status	Published - 31 Mar 2008

Keywords

Hydroaminomethylation
Hydroformylation
Limonene
Secondary amines
Terpenes
Tertiary amines

ASJC Scopus subject areas

Catalysis
General Chemistry
Process Chemistry and Technology

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10.1016/j.catcom.2007.10.008

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@article{e8c508e203e9463bb0039b63062ee3ff,

title = "One-pot synthesis of secondary and tertiary amines from R(+)-limonene by tandem hydroformylation/reductive amination (hydroaminomethylation)",

abstract = "In this work, we were able to synthesize, in good isolated yields, seven R(+)-limonene derived amines (five of that described for the first time) employing a rhodium catalysed hydroaminomethylation reaction. This protocol consists in an one-pot three step reaction: double bond hydroformylation, aldehyde/amine condensation and imine/enamine hydrogenation. Hydroaminomethylation, besides the high yields, has a high atom economy because just 1 mol of water is wasted per mol of limonene. Due to our catalytic optimizations, the reaction time was reduced from 48 h (described in the literature) to 10-24 h, as well as limonene isomerization was strongly minimized by the triphenylphosphine added.",

keywords = "Hydroaminomethylation, Hydroformylation, Limonene, Secondary amines, Terpenes, Tertiary amines",

author = "Graebin, \{Cedric S.\} and Eifler-Lima, \{Vera Lucia\} and \{da Rosa\}, \{Ricardo G.\}",

year = "2008",

month = mar,

day = "31",

doi = "10.1016/j.catcom.2007.10.008",

language = "English",

volume = "9",

pages = "1066--1070",

number = "6",

}

One-pot synthesis of secondary and tertiary amines from R(+)-limonene by tandem hydroformylation/reductive amination (hydroaminomethylation). / Graebin, Cedric S.; Eifler-Lima, Vera Lucia; da Rosa, Ricardo G. (Lead / Corresponding author).
In: Catalysis Communications, Vol. 9, No. 6, 31.03.2008, p. 1066-1070.

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

TY - JOUR

T1 - One-pot synthesis of secondary and tertiary amines from R(+)-limonene by tandem hydroformylation/reductive amination (hydroaminomethylation)

AU - Graebin, Cedric S.

AU - Eifler-Lima, Vera Lucia

AU - da Rosa, Ricardo G.

PY - 2008/3/31

Y1 - 2008/3/31

N2 - In this work, we were able to synthesize, in good isolated yields, seven R(+)-limonene derived amines (five of that described for the first time) employing a rhodium catalysed hydroaminomethylation reaction. This protocol consists in an one-pot three step reaction: double bond hydroformylation, aldehyde/amine condensation and imine/enamine hydrogenation. Hydroaminomethylation, besides the high yields, has a high atom economy because just 1 mol of water is wasted per mol of limonene. Due to our catalytic optimizations, the reaction time was reduced from 48 h (described in the literature) to 10-24 h, as well as limonene isomerization was strongly minimized by the triphenylphosphine added.

AB - In this work, we were able to synthesize, in good isolated yields, seven R(+)-limonene derived amines (five of that described for the first time) employing a rhodium catalysed hydroaminomethylation reaction. This protocol consists in an one-pot three step reaction: double bond hydroformylation, aldehyde/amine condensation and imine/enamine hydrogenation. Hydroaminomethylation, besides the high yields, has a high atom economy because just 1 mol of water is wasted per mol of limonene. Due to our catalytic optimizations, the reaction time was reduced from 48 h (described in the literature) to 10-24 h, as well as limonene isomerization was strongly minimized by the triphenylphosphine added.

KW - Hydroaminomethylation

KW - Hydroformylation

KW - Limonene

KW - Secondary amines

KW - Terpenes

KW - Tertiary amines

UR - https://www.scopus.com/pages/publications/39349113833

U2 - 10.1016/j.catcom.2007.10.008

DO - 10.1016/j.catcom.2007.10.008

M3 - Article

AN - SCOPUS:39349113833

SN - 1566-7367

VL - 9

SP - 1066

EP - 1070

JO - Catalysis Communications

JF - Catalysis Communications

IS - 6

ER -

One-pot synthesis of secondary and tertiary amines from R(+)-limonene by tandem hydroformylation/reductive amination (hydroaminomethylation)

Abstract

Keywords

ASJC Scopus subject areas

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