Journal
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
Volume 74, Issue 11, Pages 1098-1107Publisher
SOC SYNTHETIC ORGANIC CHEM JPN
DOI: 10.5059/yukigoseikyokaishi.74.1098
Keywords
C-Si bond formation; group 14 compounds; cross-coupling; palladium; rhodium; platinum; samarium; sigma-pi conjugation; photoluminescence; surface functionalization; self-assembled mono layer
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Funding
- CREST from JST
- Tokyo Kasei Chemical Promotion Foundation
- Nippon Sheet Glass Foundation for Materials Science and Engineering
- Precise Measurement Technology Promotion Foundation [15K05604]
- Ministry of Education, Culture, Sports, Science, and Technology, Japan [26110505, 26110506, 16H00957, 16H00958]
- Grants-in-Aid for Scientific Research [16H00957, 26110506, 26220801, 16H00958] Funding Source: KAKEN
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Extensive investigation of functional organosilicon and organogermanium compounds has identified various valuable applications in organic chemistry and advanced materials. This review summarizes the major developments of metal-mediated coupling reactions between group 14 hydrides and organic halides during the last decade with an emphasis on our own studies. High reactivity and selectivity have been achieved for C-Si and C-Ge bond formations under mild conditions. This transformation shows good functional group compatibility, and can serve as a powerful tool for the synthesis of medicinal, pharmaceutical, agrochemical, electrical, and photoluminescent compounds. Ground- and excited-state properties of fluorescence materials have been investigated by DFT and TD-DFT calculations, and several important aspects of the experimental observations have been validated. Direct functionalization of H-terminated Si and Ge surfaces has been demonstrated utilizing Pd-mediated arylation reactions, illustrating the potential for further development of the Pd-catalyzed reactions for the organic modification of semiconductor surfaces.
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