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Perrhenate Esters In New Catalytic Reactions

S. Bellemin-Laponnaz
Published 2009 · Chemistry

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There has been tremendous interest in the use of alkyltrioxorhenium complexes as catalysts for various organic transformations. Although such applications are now well known and, indeed, have been widely studied, other organorhenium oxide families, namely the perrhenate esters O3ReOR, have received much less attention. In this review, such ReVII species are shown to be very promising catalysts and several recent examples are presented, with the aim of shedding light on their synthetic potential as a new tool for organic chemists.
This paper references
10.1002/CHIN.197743083
USE OF OXO‐METALLIC DERIVATIVES IN ISOMERIZATION. REACTIONS OF UNSATURATED ALCOHOLS
P. Chabardes (1977)
10.1021/JA0714742
Methylrhenium trioxide revisited: mechanisms for nonredox oxygen insertion in an M-CH3 bond.
J. Gonzales (2007)
10.1002/ANIE.200604333
The oxorhenium(VII)-catalyzed direct condensation of phosphoric acid with an alcohol.
A. Sakakura (2007)
Heteroacylative ring - opening dimerization of tetrahydrofuran . Scheme 14 . Proposed mechanism for heteroacylative ring - opening dimerization of tetrahydrofuran
H. Gisie (2009)
10.1016/S0040-4039(99)02352-7
Isomerization of allylic silyl ethers catalyzed by ReO3(OSiR3) complexes
S. Bellemin-Laponnaz (2000)
phosphoric acid diesters synthesis
a A. Sakakura (2007)
10.1021/IC00075A041
Multiple bonds between transition metals and main-group elements. 124. Structures and reactivity of acylperrhenates
W. Herrmann (1993)
10.1021/OL052620G
Synthetic studies on amphidinolide B1.
Amit K. Mandal (2006)
several compounds of general formula O3ReOR by using a transesterification procedure, see
Wilkinson (1984)
10.1248/CPB.30.881
Synthesis of 3-(dialkylamino)indolizines. Reaction of 3-(2-pyridyl)-2-propenals with secondary amines.
Y. Abe (1982)
10.1246/BCSJ.80.400
Perrhenic Acid-Catalyzed Dehydration from Primary Amides, Aldoximes, N-Monoacylureas, and α-Substituted Ketoximes to Nitrile Compounds
Yoshiro Furuya (2007)
We note that the perrhenate active species may be generated from Re-O 3 OSiR 3 complexes but also more simply from rhenium oxide Re 2 O 7 , as well as from aqueous perrhenic acid ReO 3 OH
10.2174/138527207781024067
The Prins Reaction: Advances and Applications
Isidro M. Pastor and Miguel Yus (2007)
10.1021/JA054449+
Divergent enantioselective synthesis of (-)-galanthamine and (-)-morphine.
B. Trost (2005)
10.1021/CR9703212
Rhenium(VII) Oxo and Imido Complexes: Synthesis, Structures, and Applications.
Carlos C. Romão (1997)
10.1002/ANGE.200703017
Kostengünstige, effiziente und umweltfreundliche Synthese des vielseitigen Katalysators Methyltrioxorhenium (MTO)
W. A. Herrmann (2007)
400-406; c) For an example of the use of this methodology in synthesis
Y Furuya (2002)
10.1002/anie.200802575
Facile oxy-functionalization of a nucleophilic metal alkyl with a cis-dioxo metal species via a (2+3) transition state.
Brian L. Conley (2008)
10.1021/ol8019204
Rhenium(VII) catalysis of Prins cyclization reactions.
K. Tadpetch (2008)
10.1021/JA044054A
Highly selective 1,3-isomerization of allylic alcohols via rhenium oxo catalysis.
Christie Morrill (2005)
Weinheim www.chemcatchem.org 14785-14803; c)
-Vch Verlag Wiley (2006)
For other applications in total synthesis of rhenium-catalyzed isomerization of allylic alcohols, see: a)
B M Trost (2000)
10.1039/DT9840002695
Trioxorhenium(VII) alkoxides, di-isopropylamides, carboxylates and related compounds
P. Edwards (1984)
10.1021/OM971115N
1,3-Transposition of Allylic Alcohols Catalyzed by Methyltrioxorhenium
J. Jacob (1998)
10.1021/OL061072J
Approach to the synthesis of cladiell-11-ene-3,6,7-triol.
John M. Hutchison (2006)
10.1021/JO061436L
Rhenium-catalyzed 1,3-isomerization of allylic alcohols: scope and chirality transfer.
Christie Morrill (2006)
10.1002/ANGE.19971090915
MECHANISTISCHE EINBLICKE IN DIE HOCHEFFIZIENTE, REO3(OSIR3)-KATALYSIERTE ISOMERISIERUNG VON ALLYLALKOHOLEN
S. Bellemin-Laponnaz (1997)
10.1021/JA062417W
Facile functionalization of a metal carbon bond by O-atom transfer.
Brian L. Conley (2006)
10.1002/1521-3773(20020816)41:16<2983::AID-ANIE2983>3.0.CO;2-X
Rhenium(VII) oxo complexes as extremely active catalysts in the dehydration of primary amides and aldoximes to nitriles.
K. Ishihara (2002)
10.1021/JA0620639
Regiochemical control in the metal-catalyzed transposition of allylic silyl ethers.
E. Hansen (2006)
10.1002/(SICI)1521-3765(19990104)5:1<57::AID-CHEM57>3.0.CO;2-B
Mechanism of the Allylic Rearrangement of Allyloxo Metal Oxo Complexes: An Ab Initio Theoretical Investigation
S. Bellemin-Laponnaz (1999)
10.1016/J.CATCOM.2006.10.023
Perrhenic acid as catalyst for hydrosilylation of aldehydes and ketones and dehydrogenative silylation of alcohols
P. M. Reis (2007)
For other applications in total synthesis of rhenium-catalyzed isomerization of allylic alcohols
B. M. Trost (2000)
Wilkinson and Edwards synthesized in 1984 several compounds of general formula O 3 ReOR by using a transesterification procedure
10.1016/J.JORGANCHEM.2004.08.018
Methyltrioxorhenium and its applications in olefin oxidation, metathesis and aldehyde olefination
F. E. Kühn (2004)
10.1021/JA964273Z
TANDEM OXIDATIVE CYCLIZATION WITH RHENIUM OXIDE. TOTAL SYNTHESIS OF 17,18-BISEPI-GONIOCIN
S. Sinha (1997)
Wilkinson and Edwards synthesized in 1984 several compounds of general formula O 3 ReOR by using a transesterification procedure , see : a ) P . Edwards , G . Wilkinson
J. M. Gonzales (1984)
10.1002/asia.200800365
Total synthesis of (-)-apratoxin A, 34-epimer, and its oxazoline analogue.
Yoshitaka Numajiri (2009)
10.1016/S1631-0748(02)01371-1
Metal oxo complexes as catalysts for the isomerisation of allylic alcohols
S. Bellemin-Laponnaz (2002)
10.1021/JA002231B
Enantioselective Total Synthesis of (−)-Galanthamine
B. M. T. and (2000)
10.1002/ANIE.200703017
A cheap, efficient, and environmentally benign synthesis of the versatile catalyst methyltrioxorhenium (MTO).
W. Herrmann (2007)
10.1016/S0040-4039(97)10619-0
A simple and efficient method for the preparation of pyridine-N-oxides II
C. Copéret (1998)
10.1021/ol801859c
Mild and efficient Re(VII)-catalyzed synthesis of 1,1-dihydroperoxides.
P. Ghorai (2008)
Ishihara et al. also succeeded in phosphoric acid diesters synthesis; see: b)
A Sakakura (2007)
10.1002/cmdc.200600152
Investigating Carboxylic Acid Analogues of Ambruticin through Semi‐Synthesis
Y. Xu (2006)
10.1002/CHIN.199730247
Reactions Catalyzed by Methylrhenium Trioxide
J. Espenson (1997)
as such, have been widely reviewed
C Copøret (1998)
Pruckmayr, Encyclopedia of Polymer Science and Engineering, 2 ed
P. Dreyfuss (1989)
10.1002/MED.10066
Synthetic peroxides as antimalarials
Yuanqing Tang (2004)
10.1016/S0010-8545(03)00058-4
Transition metal mediated oxygen transfer to organo nitrogen compounds
W. R. Thiel (2003)
10.1021/ol8023874
Broadly applicable synthesis of 1,2,4,5-tetraoxanes.
P. Ghorai (2009)
10.1021/CR020471Z
Metal-catalyzed epoxidations of alkenes with hydrogen peroxide.
B. S. Lane (2003)
10.1021/jo801404u
Asymmetric synthesis of 6'-hydroxyarenarol: the proposed biosynthetic precursor to popolohuanone E.
Rachel H. Munday (2008)
10.1021/JA0668668
Rhenium(VII) oxide catalyzed heteroacylative ring-opening dimerization of tetrahydrofuran.
H. Lo (2007)
10.1016/0040-4020(77)84059-3
Use of oxo-metallic derivatives in isomerisation
P. Chabardes (1977)
10.1021/OM049669V
Allylic Alcohol Isomerization and Mechanistic Considerations with CH3ReO3
G. Wang (2004)
10.1002/ANIE.199709761
MECHANISTIC INSIGHTS INTO THE VERY EFFICIENT REO3OSIR3-CATALYZED ISOMERIZATION OF ALLYL ALCOHOLS
S. Bellemin-Laponnaz (1997)
Note that perrhenic acid and rhenium oxide were found to catalyze the hydrosilylation of aldehydes and ketones and the dehydrogenative silylation of alcohols; see: a)
P M Reis (2005)
Proposed mechanism for heteroacylative ring-opening dimerization of tetrahydrofuran
(2009)
10.1016/J.JORGANCHEM.2007.09.015
Immobilization of organorhenium(VII) oxides
Kavita R. Jain (2007)
10.1021/IC951508J
Multiple Bonds Between Main Group Elements and Transition Metals. 151. 1 Trioxorhenium(VII) Alkoxide Complexes
W. A. Herrmann (1997)
10.1002/ANIE.200702999
Oxidative cleavage in the construction of complex molecules: synthesis of the leucascandrolide A macrolactone.
H. H. Jung (2007)
10.1016/J.MOLCATA.2005.04.030
Reduction of carbonyl groups by high-valent rhenium oxides
B. Royo (2005)
10.3987/COM-08-S(N)58
SELECTIVE SYNTHESIS OF CYCLIC PHOSPHORIC ACID DIESTERS THROUGH OXORHENIUM(VII)-CATALYZED DEHYDRATIVE CONDENSATION OF PHOSPHORIC ACID WITH ALCOHOLS
K. Ishihara (2008)



This paper is referenced by
10.1039/C1SC00570G
Stereoselective heterocycle synthesis through a reversible allylic alcohol transposition and nucleophilic addition sequence
Youwei Xie (2011)
10.1002/anie.201208132
Cascade approach to stereoselective polycyclic ether formation: epoxides as trapping agents in the transposition of allylic alcohols.
Youwei Xie (2013)
10.1016/J.TETLET.2017.01.066
A Re2O7 catalyzed cycloetherification of monoallylic diols
X. Wan (2017)
10.1021/jo300706b
Direct substitution of hydroxy group of π-activated alcohols with electron-deficient amines using Re2O7 catalyst.
B. G. Das (2012)
10.1021/jo4028598
Chemoselective C-benzylation of unprotected anilines with benzyl alcohols using Re2O7 catalyst.
R. Nallagonda (2014)
10.1002/CHIN.201007218
Perrhenate Esters in New Catalytic Reactions
S. Bellemin-Laponnaz (2010)
10.3762/bjoc.11.114
Novel carbocationic rearrangements of 1-styrylpropargyl alcohols
Christine Basmadjian (2015)
10.1039/c3ob40918j
Stereoselective direct reductive amination of ketones with electron-deficient amines using Re2O7/NaPF6 catalyst.
B. G. Das (2013)
10.1021/acs.jpclett.6b00754
Two Spin-State Reactivity in the Activation and Cleavage of CO2 by [ReO2](.).
Valentino Canale (2016)
10.1002/anie.201402010
Heterocycle synthesis based on allylic alcohol transposition using traceless trapping groups.
Youwei Xie (2014)
10.1039/c8sc03570a
Diarylmethane synthesis through Re2O7-catalyzed bimolecular dehydrative Friedel–Crafts reactions† †Electronic supplementary information (ESI) available: Experimental protocols and spectral data. See DOI: 10.1039/c8sc03570a
Q. Qin (2018)
10.1002/anie.201705924
Re2 O7 -Mediated Dehydrative Cyclization Reactions: Total Synthesis of Herboxidiene and Its 12-Desmethyl Analogue.
Tyler M Rohrs (2017)
10.1002/9783527809080.cataz14392
rhenium in catalysis
R. Fischer (2020)
10.3762/bjoc.9.174
Re2O7-catalyzed reaction of hemiacetals and aldehydes with O-, S-, and C-nucleophiles
W. Sittiwong (2013)
10.1039/C5RA04931H
Re2O7 catalyzed dienone-phenol rearrangement
Zilei Xia (2015)
10.1039/c2cc15472b
Re2O(7)-catalyzed three-component synthesis of protected secondary and tertiary homoallylic amines.
S. Pramanik (2012)
10.1039/C6RA10399E
Tandem allylic alcohol isomerization/oxo-Michael addition reaction promoted by Re2O7
J. Hu (2016)
10.1039/c2cc33185c
The direct reductive amination of electron-deficient amines with aldehydes: the unique reactivity of the Re2O7 catalyst.
B. G. Das (2012)
10.1021/OM300852S
Homogeneous Model Complexes for Supported Rhenia Metathesis Catalysts
Yu-Ying Lai (2012)
10.1002/chem.201501423
Evolution of a Unified Strategy for Complex Sesterterpenoids: Progress toward Astellatol and the Total Synthesis of (-)-Nitidasin.
Daniel T. Hog (2015)
10.1002/chem.201501914
Synthesis of air- and moisture-stable, storable chiral oxorhenium complexes and their application as catalysts for the enantioselective imine reduction.
B. G. Das (2015)
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