Special Topic - Thieme · Special Topic. Reviews and Full Papers in Chemical Synthesis January 19,...
Transcript of Special Topic - Thieme · Special Topic. Reviews and Full Papers in Chemical Synthesis January 19,...
Reviews and Full Papers in Chemical Synthesis
January 19, 2021 • Vol. 53, 193–390
2Synthesis of Peripherally Arylated Tetrathiafulvalenes Extended with an Anthraquinoid Spacer via Pd-Catalyzed C–H Arylation and Construction of a Double-Helical Cobalt-Based Metal-Organic Framework
A. Yoshimura, K. Henmi, H. Kimura, R. Sakakibara, R. Ochi, T. Shirahata, H. Yorimitsu, Y. Misaki
Special TopicFunctional Organic MoleculesEditor: Franziska Schoenebeck
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Reviews and Full Papers in Chemical Synthesis
2021Vol. 53, No. 2
January IISynthesis
Synthesis
Cover Design: © Thieme
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Synthesis 2021, 53, 193–214DOI: 10.1055/s-0040-1705939
S. PonraB. BoudetP. Phansavath*V. Ratovelomanana-Vidal*Chimie ParisTech-CNRS, France
Synthesis
as
Recent Developments in Transition-Metal-Catalyzed Asymmetric Hydrogenation of Enamides
H2
Rh
IrRu
Ni Co
OH
NHAcR
CO2Me
NHAc
ArCHO
NHAc
NHAc
PR22
R1
O
NHAc
R2
R1
CNAcHN
R
NH
O
OR
N
HN R
O
Ph
*
AcHN
Ar
O
OR
OR
NBn
O
CO2H( )n
CF3
NHAcR
CO2Me
NHAc
R2
R1
R3
NPh
R
O
SO2R2NHAc
R1
NO2
NHAc
R
NHAc
R
NHAc
OMOM
R1
R2F
CO2R'
NHAc
R
Ar
HN
O
*R NHAc
R
*
© 2021. Thieme. All rights reserved.
Review
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Synthesis 2021, 53, 215–237DOI: 10.1055/s-0040-1707298
L. Carceller-FerrerG. BlayJ. R. Pedro*C. Vila*Universitat de València, Spain
Recent Advances in Catalytic Enantioselective Synthesis of Pyrazolones with a Tetrasubstituted Stereogenic Center at the 4-Position
AsymmetricNucleophilic
pathway
NN
PhO
Y
Me
NN
R1
O
X
R2
Y
AsymmetricElectrophilic
pathway
NN
PhO
Y
Me
N
N
PhO
Me
R
AsymmetricElectrophilic-Nucleophilic
pathway
Review
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pro
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Synthesis 2021, 53, 238–254DOI: 10.1055/s-0040-1707268
F. ZhangL. XinY. YuS. Liao*X. Huang*Fujian Province University, P. R. of ChinaFujian Institute of Research on the Structure of Matter, P. R. of China
Synthesis
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is s
t
Recent Advances in Palladium-Catalyzed Bridging C–H Activation by Using Alkenes, Alkynes or Diazo Compounds as Bridging Reagents
nArPdn
thermodynamicallystable palladacycle
Ar
C–H bondactivation
H
Pd
nAr
n = 0, 1
alkene
alkyne
diazocompound
H
nAr
R1
Pd
R2
H
nAr
R1
Pd
R2
ArPd
R1 R2
O
H
S
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hort Review
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Synthesis 2021, 53, 255–266DOI: 10.1055/s-0040-1707270
T. EdlováM. ČubiňákT. Tobrman*University of Chemistry and Technology, Prague, Czech Republic
as
Cross-Coupling Reactions of Double or Triple Electrophilic Templates for Alkene Synthesis
(R)X
X(R)
OFG
X(R) R
RR
R
R B(OH)2
RBu3Sn
R MgX
R ZnX+
X = F, Cl, Br
chemo- and stereoselectivetransformations
OFG = OTs, OTf, OC(O)R, OP(O)(OR)2
TM-cat
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Synthesis 2021, 53, 267–278DOI: 10.1055/s-0040-1707269
C. BandariK. M. Nicholas*University of Oklahoma, USA
Deoxygenative Transition-Metal-Promoted Reductive Coupling and Cross-Coupling of Alcohols and Epoxides
R R
R1
R1R
Ar R
O
R R1
R1 OHAr X
R1 M
R OH
R
R
R
OH
R1
R1
OH
R
R3R2
R2
R3
R1
OH
R
O
R2 R2
RR1
R
OHR2
R R1
R R1
R1
R2
S
hort Review267
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Synthesis 2021, 53, 279–295DOI: 10.1055/s-0040-1706535
Á. MagyarK. JuhászZ. Hell*Budapest University of Technol-ogy and Economics, Hungary
Synthesis
Synthesis
is s
t
The Application of 4Å Molecular Sieves in Organic Chemical Syntheses: An Overview
4A Molecular Sieves
Additive
Catalyst Co-catalystSupport
S
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hort Review
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Synthesis 2021, 53, 296–308DOI: 10.1055/s-0040-1707318
M. M. HorninkA. U. LopesL. H. Andrade*University of São Paulo, Brazil
as
Biobased Spiroimides from Itaconic Acid and Formamides: Molecular Targets for a Novel Synthetic Application of Renewable Chemicals
Feature
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Synthesis 2021, 53, 309–317DOI: 10.1055/s-0040-1707313
M. SakturaS. FrankowskiB. JoachimŁ. Albrecht*Lodz University of Technology, Poland
Aminocatalytic Synthesis of Uracil Derivatives Bearing a Bicyclo[2.2.2]octane Scaffold via a Doubly Cycloadditive Reaction Cascade
N
N
O
O
OO
R
N
NO
OCHO
R
OHCR
aminocatalyticdoubly cycloadditive
reaction cascade
NH Ph
Ph
10 examples45–86% yield
>25:1 drfrom 97:3 to >99:1 er
R = Ph, 4-BrC6H4, 4-ClC6H4, 4-O2NC6H4,4-MeC6H4, 3-MeC6H4, 2-MeC6H4, 4-MeOC6H4,
2-MeOC6H4, 2-furyl
+
Feature
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Synthesis 2021, 53, 318–325DOI: 10.1055/s-0040-1707896
A. Arjona-EstebanA. RauschM. O. VysotskyF. Würthner*Universität Würzburg, Germany
Synthesis
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is s
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Merocyanine Dyes with Extended Polymethine Chains by Simple Two-Step Condensation Sequence
O
O
O
O
MeNHOH80 °C, 20 h
pressure flask
O
ON
Bu
2-hexanone
O
N
Bu
KOAc, Ac2Or.t., 1 h
S
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pecial Topic
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Synthesis 2021, 53, 326–331DOI: 10.1055/s-0040-1707177
A. YoshimuraK. HenmiH. KimuraR. SakakibaraR. OchiT. ShirahataH. YorimitsuY. Misaki*Ehime University, Japan
as
Synthesis of Peripherally Arylated Tetrathiafulvalenes Extended with an Anthraquinoid Spacer via Pd-Catalyzed C–H Arylation and Con-struction of a Double-Helical Cobalt-Based Metal-Organic Framework
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Synthesis 2021, 53, 332–337DOI: 10.1055/s-0040-1707288
F. J. WidnerC. KieningerK. WurstE. DeeryA. D. LawrenceM. J. WarrenB. Kräutler*University of Innsbruck, Austria
Synthesis, Spectral Characterization and Crystal Structure of Chlororhodibalamin: A Synthesis Platform for Rhodium Analogues of Vitamin B12 and for Rh-Based Antivitamins B12
N
N
Cl
O
+ RhIII
N
N
R
O
+ RhIII
N
N
O
+HH
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pecial Topic332
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Synthesis
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pro
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Synthesis 2021, 53, 338–343DOI: 10.1055/s-0040-1707290
F.-Z. YanY.-G. ShaoZ. ZhangY.-F. ShenX.-C. HuangP.-L. ZhangS. Li*Hangzhou Normal University, P. R. of China
Synthesis
Synthesis
is s
t
Synthesis of Catenanes from a BMP32C10-Based Cryptand Tuned by the Linkage Length of Paraquat Salts
S
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pecial Topic
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Synthesis 2021, 53, 344–347DOI: 10.1055/s-0040-1705950
P. MeiR. KurosakiA. MatsumotoH. Yamada*N. Aratani*Nara Institute of Science and Technology (NAIST), Japan
as
One-Pot Synthesis of a Cyclic Pyrene Octamer from Two Bifunctional-ized Pyrene Monomers
tBu
pinB Bpin
tBu
I I
tBu
tBu
tBu
tBu
tBu
tBu
tBu
tBu+
Cs2CO3toluene/DMF
Pd NH2Cl
PtBu3
One-pot cyclization!
2.8%
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Synthesis 2021, 53, 348–358DOI: 10.1055/s-0040-1707278
J. O. StrelnikovaN. V. RostovskiiO. V. KhoroshilovaA. F. KhlebnikovM. S. Novikov*St. Petersburg State University, Russian Federation
An Efficient Synthesis of Functionalized 2H-1,3,5-Oxadiazines via Metal-Carbenoid-Induced 1,2,4-Oxadiazole Ring Cleavage
R2RO2C
MLn
R2RO2C
N2
MLn
O
NN
Ar/Alk
R1R2
CO2R
• 24 examples• yield up to 97%
N
OAr
RO2C
R2
N
O
N
Ar/Alk
M = Rh, Cu
R1 = H R1 ≠ H
R1
H, CN, CF3, CO2Me
H, Ar, Alk, OMe, NMe2
N4-attack N2-attack
Paper
348
X
Synthesis
rictly
pro
hibi
ted.
Synthesis 2021, 53, 359–364DOI: 10.1055/s-0040-1706551
V. LösleO. KataevaH.-J. Knölker*Technische Universität Dresden, Germany
Synthesis
Synthesis
is s
t
First Total Synthesis and Investigation of the X-ray Crystal Structure of the Pyrano[3,2-a]carbazole Alkaloid Clausenalansine A
N
H
O
CHOHO
N
H
O
HOTBDPSO
Br OMeH2N O
H+ +
koenine clausenalansine A
© 2021. Thieme. All rights reserved.
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Synthesis 2021, 53, 365–370DOI: 10.1055/s-0040-1706422
I. CasadiaT. O. DaherS. MouraD. F. BackE. FaoroC. S. SchwalmG. A. CasagrandeG. C. PaveglioL. Pizzuti*Universidade Federal da Grande Dourados, Brazil
as
A Domino Reaction for the Synthesis of Novel 1,3-Dihydrofuro-[3,4-c]pyridines from Pyridoxal and Ketones
NOH
OO
Ar
NOH
O
OH
HCl·
O
Ar+
dominoClaisen–Schmidt condensation–
oxa-Michael addition
Representative examples:
NOH
OO
NOH
OO
NOH
OO
NOH
OO
S
65% 90% 67%53%
9 compounds53–90%
room temperaturehazardless solvent
easy workupno chromatographic purification
Paper
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Synthesis 2021, 53, 371–382DOI: 10.1055/s-0040-1705941
V. A. TkachukV. O. ShishkanuT. M. TkachukS. V. ShishkinaO. V. Hordiyenko*Taras Shevchenko National Uni-versity of Kyiv, Ukraine
2-Carbamimidoylbenzoic Acid as a New Effective and Available Precur-sor for the Synthesis of Substituted 2-(Pyrimidin-2-yl)-benzoic Acids
CO2HNH2
NH
HN
N
CO2H
R1
O
OMe
O
Ar1
O
MeO
HO
Ar1
N
N
69%
Ar1 = 4-ClC6H4
CO2H
O R2 (H, CF3)MeO
O
OAr2
OMe
ON
N
R2CO2H
– Ar2OH (Ar2 = 4-ClC6H4, 2-O2NC6H4)
1,3-dielectrophile
73–82%
R1 = Me, Et, Ph, OH, NH2 (71–92%)
N
N
R1
O
O
H2O (R1 = NH2)
– H2O
R1 = Me, Et, Ph, NH2 (72–95%)
/
Paper
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XI
Synthesis
rictly
pro
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Synthesis 2021, 53, 383–390DOI: 10.1055/s-0040-1707356
X. YeJ. HuangZ. DengJ. YuanY. Peng*Jiangxi Normal University, P. R. of China
Synthesis
Synthesis
is s
t
Palladium-Catalyzed Cross-Coupling Reactions of 4-Tosyloxyquinazolines with Indoles: An Efficient Approach to 4-(1H-Indol-1-yl)quinazolines
N
N
R1
OTs
X +
N
N
R1
X
NSPhos (10 mol%)
toluene, 110 °C
Pd(TFA)2 (5 mol%)
K2CO3 (2 equiv)NH
Y
Y
26 examples
© 2021. Thieme. All rights reserved.
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