Imprimatur: Date, Signature tc1818st.fm 10/29/18Imprimatur: Date, Signature tc1818st.fm 10/29/18 Accounts and Rapid Communications in Chemical Synthesis 2018 ... Syntheses and Redox

Imprimatur:

Date, Signaturetc1818st.fm 10/29/18

Accounts andRapid Communications in Chemical Synthesis

2018Vol. 29, No. 18

NovemberSyn lett

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Synlett 2018, 29, 2331–2336DOI: 10.1055/s-0037-1610432

S. L. JohnsonL. A. CombeeM. K. Hilinski*University of Virginia, USA

Syn lett

as

Organocatalytic Atom-Transfer C(sp3)–H Oxidation

R1

R2R3

HO N

N

O N

N N

O O

O NR

catalytic

[O] or [N]

site-selectiveoxidation

i-Pr

Me H

Me

NHTs

NPhth

AcO

RMe

Me

H

H

H

OH

C–H hydroxylation

C–H amination

Synpacts

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Synlett 2018, 29, 2337–2341DOI: 10.1055/s-0037-1610550

L. ZhangY. Wang*Shandong University, P. R. of China

Uncovering Multifaceted Iodonium Ylides: Versatile Reactivity Enables Cyclization of Simple Arylamines

+

NR1OC CO2R2

IPh R

N

R1OC CO2R2

R

without modification of amineswithout a transition metalwithout additional hydrogen acceptorwithout additional initiator/oxidant

Exceptional Iodonium Ylide = Electron Transfer + Hydrogen Abstraction + Nucleophilic Addition

Synpacts

2337

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Synlett 2018, 29, 2342–2361DOI: 10.1055/s-0037-1609584

S. Kotha*K. Lahiri*G. SreevaniIndian Institute of Technology-Bombay, IndiaV. K. Krishna Menon College of Commerce & Economics, India

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Design and Synthesis of Aromatics through [2+2+2] Cyclotrimerization

Rh(

PP

h 3) 3

Cl

CpCo(

CO) 2

Mo(CO)6

OH

OHCO2Et

TsN

TMS

TMS

R

R

RO

O

O

Br

Rh(PPh3 )3 Cl

Cp*RuCl(cod) CO2Me

MeO2C

MeO2C

CO2Me

O

O

O

O

N

N

O

O

O

BocNsteps

O

O

O

O

OH

PBr3

[CpRu(C10H

8)] +Cl –

Mo(

CO

) 6

HO

OH

O

MeN

NN

Hsp90 InhibitorAT13387

Br

[2+2+2]Cycloaddition

Cl2(PPh3)2Ru=CHPh

Account

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Synlett 2018, 29, 2362–2371DOI: 10.1055/s-0037-1609907

S. P. PanchalB. K. ReddyV. G. Anand*Indian Institute of Science Edu-cation and Research, India

as

Syntheses and Redox Chemistry of Antiaromatic Core-Modified Isophlorinoids

HN

NNH

NHN

N

NH

N

OO

OO

SS

S

SO

SO

SO

HNO

O

Porphyrin N-Confused Porphyrin

Isophlorins and Confused Isophlorins

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Synlett 2018, 29, 2372–2376DOI: 10.1055/s-0037-1611000

Y. FujiwaraR. MutaK. SatoH. HaramuraY. YamadaT. Hanamoto*Saga University, Japan

A γ-Fluoro β-Acetoxypropyl Sulfonium Salt as an Equivalent of a (Fluoromethyl)vinyl Sulfonium Salt: Reagent for the Facile Synthesis of Monofluoromethylated Cyclopropanes or Aziridines

H2FCSPh2•OTf

OAc+ –

H2FC

SPh2•OTf+ –

N

Ts

H2FC

H2FC

EWG2

EWG1

EWG2

EWG1

TsNH2

transient

baseup 98% yield 9 examples

96% yield

free-flowing solid

Letter

2372

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Synlett 2018, 29, 2377–2380DOI: 10.1055/s-0037-1611024

S. WatanabeM. IshikawaT. NomuraT. FukuyamaS. Yokoshima*Nagoya University, Japan

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Total Synthesis of Lycoposerramine-R

O

Me

OH

O

MgBr

HH

O

On-Bu

Ph

S

H2N

O

OMe

HN

H

HN

H

O

lycoposerramine-R

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Synlett 2018, 29, 2381–2384DOI: 10.1055/s-0037-1610632

C. DaiY. ShenQ. Wang*East China University of Science and Technology, P. R. of China

as

Two Propanediurea-based Cucurbituril Analogues: Bis-ns-TD[8] and NH-ns-TD[4]

Letter

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Synlett 2018, 29, 2385–2389DOI: 10.1055/s-0037-1610995

M. Minakawa*K. WatanabeS. ToyodaY. UozumiYamagata University, Japan

Iridium-Catalyzed Direct Cyclization of Aromatic Amines with Diols

HN

NH2

R2

R1

+ HO OH

N

N

R2

R1

5 examples

7 examples

73–83% yield

26–76% yield

+ 2 H2O

R1 = H, OMe, Me, F, Cl

R2 = H, 4-OMe, 4-Me, 4-F, 3-F, 4-Cl, 4-CF3

+ 4 H2O

catalyst: IrCl3ligand: BINAP

mesitylene 165 °C

18 h

Letter

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Synlett 2018, 29, 2390–2395DOI: 10.1055/s-0037-1611061

L.-M. Chen*Z.-H. LiuX.-F. NieX.-Q. GuoT.-R. Kang*Chengdu University, P. R. of ChinaChina West Normal University, P. R. of China

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Straightforward Synthesis of Triester-Substituted Pyrrolizidines by a Three-Component Reaction of β,γ-Unsaturated α-Keto Esters, Proline, and Maleates

Ar

N CO2R3

CO2R3MeO2C

Ar

O

O

OR2

NH

CO2H

+

CO2R3

CO2R3DMF

80 °C14 examplesup to 86% yield and 93:7 drester groups in trans-orientationone quaternary center

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Synlett 2018, 29, 2396–2403DOI: 10.1055/s-0037-1609948

Y. Liu*Q.-L. WangB.-Q. XiongP.-L. ZhangC.-A. YangY.-X. GongJ. LiaoQ. Zhou*Hunan Institute of Science and Technology, P. R. of China

as

Visible-Light-Mediated ipso-Carbosulfonylation of Alkynes: Synthesis of 3-Sulfonylspiro[4,5]trienones from Propiolamides and Sulfonyl Chlorides under Transition-Metal-Free Conditions

+Z

N

R2

R3

O

ON

R2

R3

O

R4 S Cl

O

O

SR4

O

O

R1 R1

Z = OR, SMe, F, Cl, Br, I

Transition-metal-free

visible light

R4 = Ar, heterocyclic, aliphaticH2O

44 examples, up to 95%yield

Transition-metal-free Broad substrates scope

High yields Easily handled conditions

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Synlett 2018, 29, 2404–2407DOI: 10.1055/s-0037-1609629

T. Hirashita*Y. SugiharaS. IshikawaY. NaitoY. MatsukawaS. ArakiNagoya Institute of Technology, Japan

Revisiting Sodium Hypochlorite Pentahydrate (NaOCl·5H2O) for the Oxidation of Alcohols in Acetonitrile without Nitroxyl Radicals

OH

R2R1

O

R2R1

NaOCl (Bleach)TEMPO, KBrCH2Cl2

NaOCl·5H2OTEMPO, Bu4NHSO4CH2Cl2

NaOCl·5H2ONo CatalystCH3CN

1° > 2° 1° < 2°1° = 2°

benzylic and aliphatic secondary alcohols

NaOCl·5H2O

CH3CN up to 97% yield

10 examples

Letter

2404

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Synlett 2018, 29, 2408–2411DOI: 10.1055/s-0037-1611019

M. KatadaK. KitaharaS. IwasaK. Shibatomi*Toyohashi University of Technology, Japan

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Catalyst-Free Decarboxylative Fluorination of Tertiary β-Keto Carboxylic Acids

easily accessible to various tertiary fluoridescatalyst-free reaction

O

R1CO2H

R2 R3 – CO2

O

R1F

R2 R3N

N

F

Cl

2BF4

+–

++

14 examples56–93% yield

R1 = alkyl, arylR2, R3 = alkyl, allyl, benzyl

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Synlett 2018, 29, 2412–2416DOI: 10.1055/s-0037-1611012

Z. SiposK. Kónya*University of Debrecen, Hungary

as

Synthesis of 1,3-Azol-2-yl O-Heterocycles by Microwave-Irradiation-Assisted Direct C–H Functionalization

O

Br

ON

Y

Y = NMe, O, S MW-assisted conditions

+N

Y

25 examplesup to 88% yield

O-heterocycles:flavones,

chromone, coumarin,

chromanones

C-2 selective coupling of 1,3-azoleswith O-heterocycles

Pd catalyst

CuIDMF

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Synlett 2018, 29, 2417–2421DOI: 10.1055/s-0037-1610298

M. S. AziziJ. Cossy*PSL Research University, CNRS, France

Selective Deprotection of N-Tosyl Alkoxyamines Using Bistrifluoromethane Sulfonimide: Formation of Oxime Ethers

ONH

SO O HNTf2 (10 mol%)

CH2Cl2, 40 °C, 18 h ONR R+ H

O

R'R'

metal-free

R' = H, OMe

+ TsOH

40–73%

10 examples

R =

Ph

Letter

2417

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Synlett 2018, 29, 2422–2426DOI: 10.1055/s-0037-1611227

N. YiY. XiongQ. HuangN. YanY. XieD. LanZ. YiC.-T. AuB. Yi*J. Xiang*Hunan Institute of Engineering, P. R. of ChinaHunan University, P. R. of China

Syn lett

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Copper-Catalyzed Oxidative Self-Coupling of α-Amino Carbonyl Compounds for the Synthesis of Tetrasubstituted 1,4-Enediones

20 examplesup to 84% yield

high stereoselectivity

Cu(acac)2, DTBP

DBU, CH3CN, 100 °CPh

O

NR2

R1

N N

Ph

O

Ph

O

R1 R1

R2 R21

2, Z-isomerR1, R2 = alkyl, aryl

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Synlett 2018, 29, 2427–2431DOI: 10.1055/s-0037-1611001

N. RiemerC. CoswigM. ShipmanB. Schmidt*Universität Potsdam, Germany

as

Palladium-Catalyzed Cross-Coupling of Arenediazonium Salts with Organoindium or Organobismuth Reagents

N2 BF4 Pd-catalyzed

Organo-In reagents

Organo-Bi reagents• 22 examples• 35–92% yield• R1 = Ac, NO2, NHAc, F, OH, OCH3, Br, CN, CO2CH3

• R2 = OCH3, F

R1

R2

R1cross-coupling

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Synlett 2018, 29, 2432–2436DOI: 10.1055/s-0037-1610293

B. SunZ. YanC. Jin*W. Su*Zhejiang University of Technology, P. R. of China

(Diacetoxyiodo)benzene-Mediated Transition-Metal-Free Amination of C(sp3)–H Bonds Adjacent to Heteroatoms with Azoles: Synthesis of N-Alkylated Azoles

+

Z, Z' = C, O, S, N(Me)CO

Z Z'

H

Z Z'

NPhI(OAc)2 (1.0 equiv)

NH

Y

X

Ar

X = N, C Y = N, C

X

YArMetal-free

C–N bondHigh funtionality tolerance

25 examplesup to 96% yield

Letter

2432

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Synlett 2018, 29, 2437–2443DOI: 10.1055/s-0037-1610300

H.-S. HuangR. KongX.-A. ZhengW.-J. ChenS.-B. HanD.-Y. ZengS.-S. Gong*Q. Sun*Jiangxi Science and Technology Normal University, P. R. of China

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A Practical Method for Regioselective 5′-O-tert-Butyldimethylsilyl Deprotection of Persilylated Nucleosides by Methanolic Phosphomolybdic Acid

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Synlett 2018, 29, 2444–2448DOI: 10.1055/s-0037-1611062

X. TianY.-L. Ren*F. RenX. ChengS. ZhaoJ. Wang*Henan Normal University, P. R. of ChinaHenan University of Science and Technology, P. R. of China

as

Direct Conversion of Benzyl Ethers into Aryl Nitriles

Ar CH2OR Ar CN

NH4OAc

O2

Catalyst, 50 °C, 20 h

Letter

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