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Synfacts 2011(8): 0918-0918  
DOI: 10.1055/s-0030-1260707
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

C-C Bond-Forming Reactions in Water with Pd-PPh2-MSN

Contributor(s): Yasuhiro Uozumi, Tsubasa Muto
W. He, F. Zhang, H. Li*
Shanghai Normal University, P. R. of China
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Publication History

Publication Date:
20 July 2011 (online)

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Significance

PPh2-functionalized mesoporous silica nanospheres (PPh2-MSN) were prepared by co-condensation of TEOS and PPh2CH2CH2Si(OEt)3 in the presence of CTAB under basic conditions. The resulting PPh2-MSN was treated with PdCl2(PPh3)2 to give a MSN-supported palladium complex Pd-PPh2-MSN (eq.1). Pd-PPh2-MSN catalyzed the Barbier reaction of aryl aldehydes 1 and allyl bromide (2) with SnCl2 in water to give the corresponding products 3 in up to 95% conversion and 93% selectivity (eq. 2, 3 examples). The catalyst also promoted the Sonogashira coupling of phenyl acetylene (4) and aryl iodides (5) with CuI in the presence of DBU in water to afford the corresponding diaryl alkynes 6 in up to 97% yield (eq. 3, 4 examples).