Triphenylphosphine dibromide: a simple one-pot esterification reagent

被引：26

作者：

Salome, Christophe ^{[1
]}

Kohn, Harold ^{[1
,2
]}

机构：

[1] Univ N Carolina, Sch Pharm, Div Med Chem & Nat Prod, Chapel Hill, NC 27599 USA

[2] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA

来源：

TETRAHEDRON | 2009年 / 65卷 / 02期

关键词：

MITSUNOBU REACTION; DIRECT CONVERSION; FACILE SYNTHESIS; ALCOHOLS; ESTERS; CLEAVAGE; ACIDS; CONFIGURATION; RESOLUTION; HALIDES;

D O I：

10.1016/j.tet.2008.10.062

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a one-pot, expedient protocol for the conversion of carboxylic acids to their esters using excess triphenylphosphine dibromide, base, and the alcohol. The reaction gave the esterified product in moderate-to-high yields (30-95%). For chiral acids, the reaction proceeded with little or no racemization. Use of a chiral alcohol in this transformation gave the ester with retention of configuration of the stereogenic center. Information is presented indicating that esterification proceeds through the intermediate generation of an acyloxyalkoxyphosphorane and where steric interactions play an important role in the energetics of the reaction. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：456 / 460

页数：5

共 50 条

[1] SIMPLE ONE-POT METHOD FOR ESTERIFICATION
STADLER, PA
[J]. HELVETICA CHIMICA ACTA, 1978, 61 (05) : 1675 - 1681
[2] A Simple and One-Pot Synthesis of β-Sultams by Using the Vilsmeier Reagent
Zarei, Maaroof
Jarrahpour, Aliasghar
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (02) : 438 - 441
[3] One-pot oxidative esterification and amidation of aldehydes
Ekoue-Kovi, Kekeli
Wolf, Christian
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (21) : 6302 - 6315
[4] One-pot oxidative esterification and amidation of aldehydes
Department of Chemistry, Georgetown University, 37th and O Streets, Washington, DC 20057, United States
[J]. Chem. Eur. J, 2008, 21 (6302-6315):
[5] One-pot esterification and amidation of phenolic acids
Nakamura, Kozo
Nakajima, Takero
Aoyama, Toshifumi
Okitsu, Sho
Koyama, Masahiro
[J]. TETRAHEDRON, 2014, 70 (43) : 8097 - 8107
[6] In a simple one-pot reaction
Saalfrank, R.W.
Burak, R.
Breit, A.
Stalke, D.
Herbst-Irmer, R.
Daub, J.
Porsch, M.
Bill, E.
Muther, M.
Trautwcin, A.X.
[J]. Angewandte Chemie (International Edition in English), 1994, 33 (15-16): : 1621 - 1623
[7] Triphenylphosphine Catalyzed, One-Pot, Multicomponent Synthesis of Spirooxindoles
Riyaz, Syed
Naidu, A.
Dubey, Pramod K.
[J]. LETTERS IN ORGANIC CHEMISTRY, 2012, 9 (02) : 101 - 105
[8] A NEW REAGENT FOR A ONE-POT CYCLOPENTENONE ANNELATION
WELCH, SC
ASSERCQ, JM
LOH, JP
[J]. TETRAHEDRON LETTERS, 1986, 27 (10) : 1115 - 1118
[9] A Practical One-Pot Transformation of Triphenylphosphine Oxide to Triphenylphosphine by Reduction of in situ Generated Triphenylphosphine Dichloride
Yano, Tomotake
Hoshino, Masakatsu
Kuroboshi, Manabu
Tanaka, Hideo
[J]. SYNLETT, 2010, (05) : 801 - 803
[10] Triphenylphosphine dibromide: A useful reagent for conversion of aldoximes into nitriles
Darvish, Fatemeh
Movassagh, Barahman
Erfani, Masoud
[J]. ARABIAN JOURNAL OF CHEMISTRY, 2015, 8 (06) : 865 - 867

← 1 2 3 4 5 →