Tributylphosphine, excellent organocatalyst for conjugate additions of non-nucleophilic N-containing compounds

Carolina Gimbert; Marcial Moreno-Mañas; Elisabet Pérez; Adelina Vallribera

doi:10.1016/j.tet.2007.05.088

Tributylphosphine, excellent organocatalyst for conjugate additions of non-nucleophilic N-containing compounds

Carolina Gimbert, Marcial Moreno-Mañas, Elisabet Pérez, Adelina Vallribera

Department of Chemistry

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

51 Citations (Scopus)

Abstract

Conjugate additions of non-nucleophilic N-containing compounds such as amides, thioamides, sulfonamides, and electron-poor anilines with different Michael acceptors can be promoted through the use of tributylphosphine. The range of useful pKa's of nucleophiles has been established (pKa<25) and new insights into the mechanism proposed. © 2007 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	8305-8310
Journal	Tetrahedron
Volume	63
Issue number	34
DOIs	https://doi.org/10.1016/j.tet.2007.05.088
Publication status	Published - 20 Aug 2007

Keywords

C-N bond
Conjugate addition
Mechanism
Organocatalyst
Phosphine

Access to Document

10.1016/j.tet.2007.05.088

Cite this

@article{f5eb807e6f6b4886a1b1ded461e0b80a,

title = "Tributylphosphine, excellent organocatalyst for conjugate additions of non-nucleophilic N-containing compounds",

abstract = "Conjugate additions of non-nucleophilic N-containing compounds such as amides, thioamides, sulfonamides, and electron-poor anilines with different Michael acceptors can be promoted through the use of tributylphosphine. The range of useful pKa's of nucleophiles has been established (pKa<25) and new insights into the mechanism proposed. {\textcopyright} 2007 Elsevier Ltd. All rights reserved.",

keywords = "C-N bond, Conjugate addition, Mechanism, Organocatalyst, Phosphine",

author = "Carolina Gimbert and Marcial Moreno-Ma{\~n}as and Elisabet P{\'e}rez and Adelina Vallribera",

year = "2007",

month = aug,

day = "20",

doi = "10.1016/j.tet.2007.05.088",

language = "English",

volume = "63",

pages = "8305--8310",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "34",

}

TY - JOUR

T1 - Tributylphosphine, excellent organocatalyst for conjugate additions of non-nucleophilic N-containing compounds

AU - Gimbert, Carolina

AU - Moreno-Mañas, Marcial

AU - Pérez, Elisabet

AU - Vallribera, Adelina

PY - 2007/8/20

Y1 - 2007/8/20

N2 - Conjugate additions of non-nucleophilic N-containing compounds such as amides, thioamides, sulfonamides, and electron-poor anilines with different Michael acceptors can be promoted through the use of tributylphosphine. The range of useful pKa's of nucleophiles has been established (pKa<25) and new insights into the mechanism proposed. © 2007 Elsevier Ltd. All rights reserved.

AB - Conjugate additions of non-nucleophilic N-containing compounds such as amides, thioamides, sulfonamides, and electron-poor anilines with different Michael acceptors can be promoted through the use of tributylphosphine. The range of useful pKa's of nucleophiles has been established (pKa<25) and new insights into the mechanism proposed. © 2007 Elsevier Ltd. All rights reserved.

KW - C-N bond

KW - Conjugate addition

KW - Mechanism

KW - Organocatalyst

KW - Phosphine

U2 - 10.1016/j.tet.2007.05.088

DO - 10.1016/j.tet.2007.05.088

M3 - Article

SN - 0040-4020

VL - 63

SP - 8305

EP - 8310

JO - Tetrahedron

JF - Tetrahedron

IS - 34

ER -

Tributylphosphine, excellent organocatalyst for conjugate additions of non-nucleophilic N-containing compounds

Abstract

Keywords

Access to Document

Fingerprint

Cite this