Jun 17, 2011 - NAGESWAR* (INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY, HYDERABAD, INDIA). Copper Oxide Nanoparticles Catalyzed Synthesis of ...
C a te go r y
K . H . V. R E D D Y , V. P. R E D D Y , J . S H A N K A R , B . M A D H A V , B . S . P. A . K U M A R , Y. V. D . N A G E S W A R * ( I N D I A N I N S T I T U T E O F C H E M I C A L TE C H N O L O G Y, H Y D E R A B A D , I N D I A )
Polymer-Supported Synthesis
Copper Oxide Nanoparticles Catalyzed Synthesis of Aryl Sulfides via Cascade Reaction of Aryl Halides with Thiourea Tetrahedron Lett. 2011, 52, 2679-2682.
K e y w ord s
aryl halides
Synthesis of Aryl Sulfides with Copper Oxide Nanoparticles
thioureas aryl sulfides copper oxide
nano-CuO (5.0 mol%) Cs2CO3 (2.0 equiv), N2
S X +
Ar
NH2
H2N
1
Ar
DMSO, 110 °C, 15 h
2
(2.0 mmol)
S
Ar
3
(1.2 mmol)
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Selected examples: X=I S
S
S
3c 96% yield
3b 93% yield
NO2
S
OMe
MeO 3a 97% yield
O2N
3d 87% yield
X = Br, 73% yield, 24 h
X = Br, 70% yield, 24 h S
S
S
S H2N
NH2
F3C
CF3
3e 85% yield
S 3g 88% yield
3f 82% yield
S 3h 83% yield
X = Br, 59% yield, 24 h S
N
S
N
HO
S
OH
S
N N H
N H 3i 75% yield
N
N 3j 78% yield
Significance: Copper oxide nanoparticles (33 nm, 29 m2/g) catalyzed the coupling of aromatic halides 1 and thiourea (2 ) to give the corresponding symmetrical diaryl sulfides 3 in up to 97% yield (20 examples). For the formation of 3a, the catalyst was recovered by centrifugation and reused four times without significant loss of activity (1st reuse: 97% yield; 4th reuse: 89% yield).
N 3k 79% yield
N N
3l X = Br, 60% yield, 24 h
Comment: Thiourea was used as a sulfur source, which has an advantage of avoiding volatile, foulsmelling and toxic thiols.
Yasuhiro Uozumi, Haifeng Zhou Synfacts 2011, 7, 0799-0799 Publishedonline:x .x .201 Published online: 17.06.2011 DOI: 10.1055/s-0030-1260529; Reg-No.: Y05311SF © Georg Thieme Verlag Stuttgart · New York
SYNFACTS Contributors:
2011 © THIEME STUTTGART • NEW YORK
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