Synthesis 2015; 47(23): 3645-3668
DOI: 10.1055/s-0035-1560646
short review
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in Transition-Metal-Catalyzed Silylations of Arenes with Hydrosilanes: C–X Bond Cleavage or C–H Bond Activation­ Synchronized with Si–H Bond Activation

Zheng Xu*
a   Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, No 1378, Wenyi West Road, Science Park of HZNU, Hangzhou, P. R. of China   eMail: zhengxu@hznu.edu.cn   eMail: liwenxu@hznu.edu.cn
,
Wei-Sheng Huang
a   Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, No 1378, Wenyi West Road, Science Park of HZNU, Hangzhou, P. R. of China   eMail: zhengxu@hznu.edu.cn   eMail: liwenxu@hznu.edu.cn
,
Jin Zhang
a   Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, No 1378, Wenyi West Road, Science Park of HZNU, Hangzhou, P. R. of China   eMail: zhengxu@hznu.edu.cn   eMail: liwenxu@hznu.edu.cn
,
Li-Wen Xu*
a   Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, No 1378, Wenyi West Road, Science Park of HZNU, Hangzhou, P. R. of China   eMail: zhengxu@hznu.edu.cn   eMail: liwenxu@hznu.edu.cn
b   State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, P. R. of China
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Publikationsverlauf

Received: 31. Juli 2015

Accepted after revision: 12. September 2015

Publikationsdatum:
08. Oktober 2015 (online)


Dedicated to Professor Xue-Long Hou on the occasion of his 60th birthday

Abstract

Arylsilanes are valuable organosilicon compounds and attract significant research interest due to their promising applications in organic synthesis. The development of aromatic C–Si cross-coupling reactions represents a major challenge in both organosilicon chemistry and organic synthesis. A number of investigations are focused on developing transition-metal-catalyzed Si–C coupling reactions due to the associated high atom economy and superior functional group compatibility. This review describes recent advances in transition-metal-catalyzed selective silylations of aryl C–H and C–X (X = halide) bonds with hydrosilanes.

1 Introduction

2 Silylation of Arenes with Hydrosilanes via Aryl C–H Bond Activation

2.1 Rhodium-Catalyzed Dehydrogenative Silylations

2.2 Iridium-Catalyzed Dehydrogenative Silylations

2.3 Ruthenium-Catalyzed Dehydrogenative Silylations

2.4 Platinum-Catalyzed Dehydrogenative Silylations

2.5 Other Transition-Metal-Catalyzed Dehydrogenative Silylations

3 Silylation of Arenes with Hydrosilanes via Aryl C–X Bond Cleavage

3.1 Palladium-Catalyzed Silylations of Aryl Halides

3.2 Rhodium-Catalyzed Silylations of Aryl Halides

3.3 Platinum-Catalyzed Silylations of Aryl Halides

4 Conclusion

 
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