SYNLETT

2105
S. B. Herzon*

Accounts and Rapid Communications in Synthetic Organic Chemistry

2011 No. 15 September II

K. Tanaka* K. Fukase S. Katsumura

D. T. Blackwell W. R. J. D. Galloway D. R. Spring*

[Si]

R R

(i) hydrosilylation R H [Si] R

[Si]

(ii) transmetalation to copper (iii) thermolytic dimerisation R R

[Si]

geometrically-defined alkenylsilanes

geometrically-defined butadienes

Letters

2140

Stereoselective Synthesis of Disubstituted Butadienes via Copper-Mediated Coupling of Alkenyl Silanes

Account

2115

Exploring a Unique Reactivity of 6p-Azaelectrocyclization to Enzyme Inhibition, Natural Products Synthesis, and Molecular Imaging: An Approach to Chemical Biology by Synthetic Chemists

Synpacts

Enantioselective Syntheses of ()-Kinamycin F and ()-Lomaiviticin Aglycon

2N

3HC

HO HO O OH O O O OH C3H OH OH
2N

nocylga nicitiviamol-)( O O OH OH

HO H HO
3HC

HO

F nicymanik-)( H O OH

2N

OH

VI

Table of Contents

Letters

2145

A. Khazaei* M. N. Soltani Rad* M. Kiani Borazjani* S. Saednia M. Kiani Borazjani D. Soudbar

Functionalization of Single-Walled Carbon Nanotubes with 4-Benzo-9crown-3 Ether

2151

P.-Y. Huang C. Kim* M.-C. Chen*

First Tetrabutylanthradithiophene (TBADT) Derivatives for Solution-Processed Thin-Film Transistors

2157

A. Kumar* V. K. Rao

Microwave-Assisted and Yb(OTf)3-Promoted One-Pot Multicomponent Synthesis of Substituted Quinolines in Ionic Liquid
3 4 OlC

2163

S. Nagarajan P. Muthuvel T. M. Das*

Facile One-Pot Synthesis of Inden-1-ol Derivatives

+iL

R
2

HO

)rab 5.5 ,W 08( WM

]4FB[]mimb[ 3)fTO(bY O R

OHC

OHC

2HN 2

R O R

+ OHC1R

Table of Contents

VII

2171

2177

A. Samarat Y. Kuninobu* K. Takai*

Synthesis of meso-Substituted Tetraarylalkynylporphyrins via RheniumCatalyzed Formation of Naphthalene Units

rA

2181

HO

HN

eM eM

uB-t

eM2OC

eM OH

eM

P. Angelov K. M. Hosamani Y.-c. Jeong M. G. Moloney* A. L. Thompson M. Yaqoob

Synthesis and Antibacterial Activity of Bicyclic LactamLactones

6)2HC(

rP-n ,uB-n2OC ,eM2OC ,tE2OC = R

2R

eM

N2tE

= R ,R

= rA

)%lom 01( SOHPISOJ )%lom 01( fTO]2)doc(rI[

C 531 ,lChP

lyniv ,rA = 2R rA ,klA = 1R

rA

rA

nZ

2R

1R

T. Shibata* H. Hirashima M. Kasagawa K. Tsuchikama K. Endo

Cationic Ir(I)-Catalyzed sp3 CH Bond Alkenylation of Ureas with Alkynes for the Synthesis of 2,3-Disubstituted Indoles

L. Zhang J.-Y. Lee N. Yamazaki S. Chiba*

Letters

2167

Copper(II)-Catalyzed Synthesis of Pyrazinones from a-Azido-N-allylamides under an Oxygen Atmosphere

N
1

)mta 1( 2O rednu C 08 ,FMD

3OC2K 2)cAO(uC .tac 2

N2tE

2N +

N
1

rA

VIII

Table of Contents

Letters

2185

D. Zhu J. Zhao Y. Wei H. Zhou*

A Simple and Efficient Protocol to 1,2,4-Substituted Pyrroles via a Sonogashira CouplingAcid-Catalyzed Cyclization
2 2

2187

2191

2195

hP

hP

4 lCeF

xulfer ,eneulot

lC

hP

hP

C. Pavlik M. D. Morton M. A. Invernale I. D. Berghorn G. A. Sotzing M. B. Smith*

Polymer-Mediated Reactions. A Nazarov-Like Cyclization

C. Pavlik M. D. Morton M. B. Smith*

Polymer-Mediated Pinacol Rearrangements

N H

xulfer ,enaxeh

%5976 ,selpmaxe 21

H N

H3OS3FC

C 08

N H

4lCeF

H N

D. Xiang X. Xin X. Liu S. Kumar D. Dong*

One-Pot Synthesis of Pyrano[2,3-b]quinolines from Enaminones under Solvent-Free Conditions

2R 3)fTO(aG 2R

C 09 eneulot

GWE = 1R

1R

HN

2)3hPP(2lCdP

.t.r ,FHT ,N3tE ,IuC

R rB HN
1

2)3hPP(2lCdP

.t.r ,FHT ,N3tE ,IuC H N

R HO
2R

rA ,klA = 1R

1R

N OH R

Table of Contents

IX

R. Thorwirth A. Stolle*

2203

R. Manzano J. M. Andrs R. Pedrosa*

Direct Experimental Evidence for the Epimerization of Diastereoisomers in the Enantioselective Organocatalyzed Michael Addition of Acetoacetates to Nitroolefins

2206

2211

2HC=HC ,3HC)HO(HC ,3HCOC = 3R OHC ,HO2HC ,2HC= ,O= ,SMDBTO ,HO ,H = 2R ,1R

M. Uosis-Martin M. F. Mahon M. Yevglevskis S. E. Lewis*

Concise Synthesis of 1,4a-Bifunctionalised Decalin Building Blocks by CH Activation of Decalin

H R

3R

2R

1R

C 05 ,eerf-tnevlos

CPAT

lC

lC

lC

K. Bahrami* M. M. Khodaei* N. Khodadoustan

TAPC-Catalyzed Synthesis of Thioethers from Thiols and Alcohols

Letters

2200

Solvent-Free Synthesis of Enamines from Alkyl Esters of Propiolic or But-2yne Dicarboxylic Acid in a Ball Mill

tsylatac

3FC

2eMN

S C3F NH

NH

2ON

eMOC H H

)S3,R2(

4:49 ot 5:59 re emit noitcaer eht no gnidneped 1:1 ot 1:3 morf rd

C2OR rA +

2ON

H eMOC
4 3

)S3,S2(

eneulot C2OR ,tsylatac rA C 02

lC

eMOC HO
2R

R2OC +
2ON

lyra = 2R lyra ,lykla = 1R

+ HS

rA R

Table of Contents

Letters

2214

2223

J. K. Augustine* A. Bombrun R. N. Atta

A Practical and Cost-Efficient, One-Pot Conversion of Aldehydes into Nitriles Mediated by Activated DMSO
N R OSMD OHC R

2228

A. J. Brouwer R. M. J. Liskamp*

A Simple Large-Scale Synthesis of Cbz-Protected Taurylsulfonyl Azide

O O spets 4 ro 3 O O

2231

OHC

S2eM .3 2O .2 1 XgMR .1

N. Charbonnet E. Riguet C. G. Bochet*

Singlet-Oxygen-Induced Rearrangement of Furan Derivatives

eM

tEO

tEO O

C 021 ,eerf-tnevlos tEO

)%lom 4( 2)fTO(nZ

eM N N dleiy llarevo %1705

3N

lyraoreteh dna lyra ,lykla = R

S. Safaei I. Mohammadpoor-Baltork* A. R. Khosropour* M. Moghadam S. Tangestaninejad V. Mirkhani

Regioselective Multicomponent Synthesis of Fully Substituted Pyrazoles and Bispyrazoles Catalyzed by Zinc Triflate

%9929

NHzbC

O h 21 ,C 0907 )viuqe 1.1( lCH HO2HN + Y +

O

2HNHN

2HNHN

lomm 005

OHC

H
+

N3H

O H

Table of Contents

XI

S. Roscales I. G. Salado A. G. Csk*

2237

M. S. Moustafa S. M. Al-Mousawi* M. H. Elnagdi*

Studies of Functionally Substituted Enamines: A New, One-Step Method for the Formation of Tetrahydroquinolinone and Nicotinonitrile Derivatives
O H = 3R ,2)2HC(O2)2HC( = 2R1R H = 3R ,5)2HC( = 2R1R rof O

2242

2245

I. R. Pottie P. R. Nandaluru G. J. Bodwell*

An Inverse Electron-Demand DielsAlder-Based Total Synthesis of Urolithin M7

O O

eM2OC

eMO

HO

HO

OeM

C31

HO

31

%51 d 2 ,C 54

lCH

OH

dleiy llarevo %84 edyhedlalycilasyxohtem-4 morf spets 8 7M nihtiloru

lC

lC

C31

C31

eMO

eM2OC

OeM

%11 h 2 ,C 0251 nZ ,)))

lC

L. Lohrey T. Murata D. Uemura H.-U. Humpf*

Synthesis of Isotopically Labeled Fusarium Mycotoxin 13C2-Moniliformin [1-Hydroxycyclobut-1-ene-3,4-dione]

Letters

2234

Regioselective 1,6-Conjugate Addition of Boronic Acids and Grignard Reagents to Dienylpyridines

)%lom 01( 2lCeF rBgM2R
3

1R

hP R

H N

4R

4R

1R

R
hP = 3R ,5)2HC( = 2R1R rof

R
HO NC NC hP O

h 3 ,xulfer enidirepipHOtE

hP

h 3 ,xulfer enidirepipHOtE

nim 06 ,.t.r nim 01 ,C 0

NC O
4 4R

hP

NC

3R

cAO4HN HOcA

3HC

1R
2R

hPOC = 3R O = 2R = 1R rof

lC lC C C31 31 lC

1R

R
hP HO

OeM..

N
CN hP

XII

Table of Contents

Letters

2248

A. Capperucci* A. DeglInnocenti* C. Tiberi

Organoselenosilane-Mediated Selective Mild Access to Selenolesters, Selenoanhydrides and Diacyl Diselenides

O
2R 1R

2253

2256

2259

NH

h 84 ,C 001 ,FMD ,3OC2sC 2)cAO(uC ,2)cAO(dP )1(

h 5.1 ,C 0 ,FH )2(

rB

HN

L. Ou Z. Shao W. Chen M. A. Giulianotti R. A. Houghten Y. Yu*

Solid-Phase Synthesis of 2,3,5,6-Tetrahydro-1H-imidazo[1,2-a]benzo[d][1,3]diazepines via Pd(OAc)2/Cu(OAc)2-Cocatalyzed Cyclization

O NC NC

5R

selpmaxe 61

4R C2OtE

1R

2R

.t.r ,eneulot

P3hP

tE2OC

NC

spets 4

CN

2HN

1R

2R

S. Guo R. Wang J. Li C. Li H. Deng X. Jia*

Triphenylphosphine-Catalyzed [3+2] Cycloaddition of Allenoate and Active Olefins: Syntheses of Spirooxindole Derivatives

uB-nOOC

%9955 morf egnar sdleiy

h 21 ,C 021 ,HOuB-n

)mta 1( OC ,N3tE PANIB-car ,2lCdP

W. Yang W. Han* W. Zhang L. Shan* J. Sun*

Efficient Carbonylation of Aryl and Heteroaryl Bromides under Atmospheric Pressure of CO

R O

eS eS

eS O

O R R

FABT

FABT )viuqe 1( SSDMH lC R

)viuqe 2( SSDMH

SMTeShP FABT rB hPeS

selpmaxe 71

O N R

Table of Contents

XIII

B.-H. Zheng C.-H. Ding X.-L. Hou*

2265

Compiled by C. McSweeney

2272

Compiled by M. Kumar

Enol Acetates

Spotlights

2270

[1,2-Bis(phenylsulfinyl)ethane]palladium Acetate

O2H +

HO

rB

]O[ ,2ONaN %lom 3

%6948 C 5351 ,NCeM

]rB[ +

HO

2rB

ria ro 2O = ]O[ ro rBH = ]rB[ R

L. Xu Y. Wang X. Wen C. Ding G. Zhang* X. Liang

Aerobic Oxybromination of Phenols Catalyzed by Sodium Nitrite under Mild Conditions

Letters
G H N rA

2262

Regio- and Enantioselective Pd-Catalyzed Allylic Amination of Monosubstituted Allylic Substrates with BocNHOMe
rA %8988 :ee 3:79 ot 11:98 = raenil/dehcnarb %3966 :sdleiy eMO coB N eMO coB N + rA O .t.r ,2lC2HC ,4OP3K xohPCOIS-)R,R( N eF xohPCOIS-)R,R( P N2tE O HO eMO + N H coB
2])lC5H3C(dP[

coB ,OeM = G

eM2OCO

rA

XIV

Table of Contents

Addenda and Errata

734

Erratum

XVII

Forthcoming Articles

Author Index
Al-Mousawi, S. M. 2237 Andrs, J. M. 2203 Angelov, P. 2181 Atta, R. N. 2223 Augustine, J. K. 2223 Bahrami, K. 2206 Berghorn, I. D. 2195 Blackwell, D. T. 2140 Bochet, C. G. 2231 Bodwell, G. J. 2245 Bombrun, A. 2223 Brouwer, A. J. 2228 Capperucci, A. 2248 Charbonnet, N. 2231 Chen, M.-C. 2151 Chen, W. 2259 Chiba, S. 2167 Csk, A. G. 2234 Das, T. M. 2163 DeglInnocenti, A. 2248 Deng, H. 2256 Ding, C. 2265 Ding, C.-H. 2262 Dong, D. 2187 Elnagdi, M. H. 2237 Endo, K. 2171 Fukase, K. 2115 Galloway, W. R. J. D. 2140 Giulianotti, M. A. 2259 Guo, S. 2256 Han, W. 2253 Herzon, S. B. 2105 Hirashima, H. 2171 Hosamani, K. M. 2181 Hou, X.-L. 2262 Houghten, R. A. 2259 Huang, P.-Y. 2151 Humpf, H.-U. 2242 Invernale, M. A. 2195 Jeong, Y.-c. 2181 Jia, K. 2256 Kasagawa, M. 2171 Katsumura, S. 2115 Khazaei, A. 2145 Khodadoustan, N. 2206 Khodaei, M. M. 2206 Khosropour, A. R. 2214 Kiani Borazjani, M. 2145 Kiani Borazjani, M. 2145 Kim, C. 2151 Kumar, A. 2157 Kumar, M. 2272 Kumar, S. 2187 Kuninobu, Y. 2177 Lee, J.-Y. 2167 Lewis, S. E. 2211 Li, C. 2256 Li, J. 2256 Liang, X. 2265 Liskamp, R. M. J. 2228 Liu, X. 2187 Lohrey, L. 2242 Mahon, M. F. 2211 Manzano, R. 2203 McSweeney, C. 2270 Mirkhani, V. 2214 Moghadam, M. 2214 Mohammadpoor-Baltork, I. 2214 Moloney, M. G. 2181 Morton, M. D. 2191, 2195 Moustafa, M. S. 2237 Murata, T. 2242 Muthuvel, P. 2163 Nagarajan, S. 2163 Nandaluru, P. R. 2245 Ou, L. 2259 Pavlik, C. 2191, 2195 Pedrosa, R. 2203 Pottie, I. R. 2245 Rao, V. K. 2157 Riguet, E. 2231 Roscales, S. 2234 Saednia, S. 2145 Safaei, S. 2214 Salado, I. G. 2234 Samarat, A. 2177 Shan, L. 2253 Shao, Z. 2259 Shibata, T. 2171 Smith, M. B. 2191, 2195 Soltani Rad, M. N. 2145 Sotzing, G. A. 2195 Soudbar, D. 2145 Spring, D. R. 2140 Stolle, A. 2200 Sun, J. 2253 Takai, K. 2177 Tanaka, K. 2115 Tangestaninejad, S. 2214 Thompson, A. L. 2181 Thorwirth, R. 2200 Tiberi, C. 2248 Tsuchikama, K. 2171 Uemura, D. 2242 Uosis-Martin, M. 2211 Wang, R 2256 Wang, Y. 2265 Wen, X. 2265 Wei, Y. 2185 Xiang, D. 2187 Xin, X. 2187 Xu, L. 2265 Yamazaki, N. 2167 Yang, W. 2253 Yaqoob, M. 2181 Yevglevskis, M. 2211 Yu, Y. 2259 Zhang, G. 2265 Zhang, L. 2167 Zhang, W. 2253 Zhao, J. 2185 Zheng, B.-H. 2262 Zhou, H. 2185 Zhu, D. 2185