accounts and rapid communications in chemical synthesis
TRANSCRIPT
Accounts and Rapid Communications in Chemical Synthesis
October 1, 2021 • Vol. 32, 1575–1674
Experimental Electrochemical Potentials of Nickel Complexes
Q. Lin, G. Dawson, T. Diao
16
ClusterModern Nickel-Catalyzed Reactions (Part II)
Editor: Ruben Martin, Guest Editor: Gary A. Molander
2021, 32 (16 ), 1575–1674T
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Imprimatur:
Date, Signature
toc.fm 9/16/21
Accounts andRapid Communications in Chemical Synthesis
2021Vol. 32, No. 16
October ISynlett Cover Design: © Thieme
Cover Image: Q. Lin et. al.
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Synlett 2021, 32, 1575–1580DOI: 10.1055/a-1503-7976
J. ZhuC. He*Southern University of Science and Technology, P. R. of China
Synlett
as
Catalytic Enantioselective Synthesis of Silicon-Stereogenic Alkoxy-silanes and Siloxanes
novel Si-stereogenic siloxanesup to 99% ee
ambient conditions atom economy
[Rh(cod)Cl]2 (1 mol%)+Si
H
H Si
H
OJosiphos (2.2 mol%)
broad scope
readily available starting materials
HO
Synpacts
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Synlett 2021, 32, 1581–1587DOI: 10.1055/a-1534-3103
K. LiZ. Sun*Tianjin University, P. R. of China
Recent Advances in Dimeric Cycloparaphenylenes as Nanotube Frag-ments
NN
N N
Synpacts
1581
VI
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ted.
Synlett 2021, 32, 1588–1605DOI: 10.1055/s-0040-1706027
B. H. Lipshutz*University of California, USA
Synlett
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Illuminating a Path for Organic Synthesis Towards Sustainability. No One Said It Would Be Easy…
Account
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Synlett 2021, 32, 1606–1620DOI: 10.1055/s-0040-1719829
Q. LinG. DawsonT. Diao*New York University, USA
as
Experimental Electrochemical Potentials of Nickel Complexes
New Tools1606
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Synlett 2021, 32, 1621–1624DOI: 10.1055/a-1282-9731
N. Ishida*Y. KaminoM. Murakami*Kyoto University, Japan
Nickel-Catalyzed -1,3-Dienylation of 1,3-Dicarbonyl Compounds with Propargylic Carbonates
R3 H
+ BocOMe
R3
cat. Ni
O OO O
R1 R2R1 R2
7 examples41–81% yield
R1, R2 = OMe, OEt, MeR3 = Me, Et, Ph, OMe
O
R1
O
H
or
O
R1
O
or
Cluster
1621
VII
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ted.
Synlett 2021, 32, 1625–1628DOI: 10.1055/a-1328-0352
Y. YeG. MaK. YaoH. Gong*Shanghai University, P. R. of China
Synlett
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is s
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Zn-Mediated Hydrodeoxygenation of Tertiary Alkyl Oxalates
Ni (cat.)R1
H
R2
R3
R1
R2
R3
O
OOMe
O MeO
O
H
60% yield, key intermediate to estrone
Zn/silane
Cluster
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Synlett 2021, 32, 1629–1632DOI: 10.1055/s-0040-1706683
P. M. KatheA. Berkefeld*I. Fleischer*Eberhard Karls University Tübin-gen, Germany
as
Nickel Hydride Catalyzed Cleavage of Allyl Ethers Induced by Isomeri-zation
RO
R OH
R : aryl, alkyl
RO
Ni-H (1 mol%) HA (1 equiv)
Ni-H : [Ni(PMe3)4H]N(SO2CF3)2
HA : TsOH•H2O
• Low catalyst loading• Non-precious, well-defined Ni-H precatalyst• >20 examples• 17–95% yields (R = aryl)• 82–95% yields (R = alkyl)
ALLYL DEPROTECTION
Cluster
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Synlett 2021, 32, 1633–1636DOI: 10.1055/a-1457-2399
B. HigginsonJ. Sanjosé-OrdunaY. GuR. Martin*Institute of Chemical Research of Catalonia (ICIQ), Spain
Nickel-Catalyzed Photodehalogenation of Aryl Bromides
Br
R Ni
H(D)
R
THF or THF-d8
this work
25 examplesup to 90%wide substrate scope
no reductant & no photocatalyst
Cluster
1633
VIII
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Synlett 2021, 32, 1637–1641DOI: 10.1055/s-0039-1690872
B. ShuaiP. Fang*T.-S. Mei*Shanghai Institute of Organic Chemistry, P. R. of China
Synlett
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Nickel-Catalyzed Favorskii-Type Rearrangement of Cyclobutanone Ox-ime Esters to Cyclopropanecarbonitriles
N LG
R3
R2 R1
NiCl2(glyme) (10 mol%)dtbbpy (10 mol%)
LiHMDS (2.0 equiv)DMF, rt, 12 h
CN
R1R3
R2
LG = p-F3CC6H4CO2
NiR3
R2 R1CN
26 examplesup to 90% yield
Cluster
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Synlett 2021, 32, 1642–1646DOI: 10.1055/a-1517-5895
S. LiuL. YangJ. TaoW. YuT. Wang*J. Fu*Jiangxi Normal University, P. R. of China
as
Nickel-Catalyzed Oxidative Transamidation of Tertiary Aromatic Amines with N-Acylsaccharins
R N
O
S
O
O O
R1 NAr
R2+
Ni, TBHPR N
O
Ar
R2
selective cleavage of C(sp3)–N bonds
R = aryl, alkyl 32 examplesup to 83% yield
R1, R2 = alkylR2 ≥ R1
Cluster
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Synlett 2021, 32, 1647–1651DOI: 10.1055/a-1523-3228
Y. XueJ. ChenP. SongY. He*S. Zhu*Nanjing University, P. R. of China
Nickel-Catalyzed Regiodivergent Reductive Hydroarylation of Styrenes
Ar1
Ar2–OTf
[Si–H]Ni-catalyzed
reductivehydroarylation
regiodivergent output
ligand B
ligand A
L
L1
L2
switch
Ar1 Ar2
H
Ar1
Ar2
H
anti-Markovnikov
Markovnikov(enantioenriched)
Cluster
1647
IX
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Synlett 2021, 32, 1652–1656DOI: 10.1055/s-0040-1720446
P. ZhangR. L. CantrellT. R. Newhouse*Yale University, USA
Synlett
Synlett
is s
t
Role of Benzylic Deprotonation in Nickel-Catalyzed Benzylic Dehydrogenation
Zn(TMP)2 [Ni]
N R2
HetR1
pre-equilibrium precedes dehydrogenation
N R2
HetR1
N R2
HetR1
ZnX
Cluster
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Synlett 2021, 32, 1657–1661DOI: 10.1055/a-1608-5693
Y. Li*G. Yin*Central South University, P. R. of ChinaWuhan University, P. R. of China
as
Bathocuproine-Enabled Nickel-Catalyzed Selective Ullmann Cross-Cou-pling of Two sp2-Hybridized Organohalides
Zn
+Br Br
Ni/BC
Ligand-Enabled, Good to Excellent Cross-Selectivity
Mild Reaction Conditions, Remarkable Functional Group Tolerance
sp2 sp2 sp2sp2
Cluster
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Synlett 2021, 32, 1662–1664DOI: 10.1055/s-0040-1707188
J. XiaoY.-W. WangZ.-P. Qiu*Y. Peng*Southwest Jiaotong University, P. R. of ChinaLanzhou University, P. R. of China
Ni-Catalyzed Intramolecular Reductive 1,2-Dicarbofunctionalization of Alkene: Facile Access to Podophyllum Lignans Core
X1
O
OMeAr
O
OO
O
O
OMeAr
Zn
X2 Ni
X1, X2 = I, Br Ar = 3,4,5-(MeO)3C6H2
(77%)
Cluster
1662
X
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Synlett 2021, 32, 1665–1669DOI: 10.1055/a-1337-6459
T. LundriganJ. P. TassoneM. Stradiotto*Dalhousie University, Canada
Synlett
Synlett
is s
t
Nickel-Catalyzed N-Arylation of Amides with (Hetero)aryl Electrophiles by Using a DBU/NaTFA Dual-Base System
+
22 examples, 70–95% 82% average yield
DBU/NaTFA, 100 °C
X
R1 het
Ni(COD)2/L (5 mol%)L = CyPAd-DalPhos
NH2R2
OHN R2
R1 hetO
X = Cl, Br, OTs, OMs
Cluster
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Synlett 2021, 32, 1670–1674DOI: 10.1055/a-1379-1584
S. WeiY. Mao*S.-L. Shi*Shanghai University of Engineer-ing Science, P. R. of ChinaShanghai Institute of Organic Chemistry, P. R. of China
as
Nickel-Catalyzed Ligand-Free Hiyama Coupling of Aryl Bromides and Vinyltrimethoxysilane
Br NiCl2(glyme) (10 mol%)TBAT (2.5 eq.)R
RSi(OMe)3Het
Het
2.0 eq.>26 examplesup to 90% yield
R = ester, ketone, aldehyde, cyanide, amide, sulfonyl, sulfonamide, morpholinyl, etc.
+DMA (0.2 M)
rt or 50 °C, 12 h
Cluster
1670
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