Copper Catalysis for Synthesizing Main-Group Organometallics Containing B, Sn or Si

The Chemical Record Volume 16 Issue 1 Page 419-434 published_at 2016-01-20
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Title ( eng )
Copper Catalysis for Synthesizing Main-Group Organometallics Containing B, Sn or Si
Creator
Source Title
The Chemical Record
Volume 16
Issue 1
Start Page 419
End Page 434
Abstract
A copper complex has proven to be a potent catalyst for forming a C–B bond via diborylation of arynes and alkynes, affording vic-diborylarenes and vic-diborylalkenes with high efficiency. A boryl-substituted organocopper species, which is intermediately generated in the diborylation, has been found to be captured by a tin or a carbon electrophile, leading to threecomponent borylstannylation or carboboration, in which C–B and C–Sn (or C) bonds are constructed simultaneously. Furthermore, reducing the Lewis acidity of the boron center with 1,8-diaminonaphthalene decisively alters the regiochemical behavior of the borylcopper species, enabling the installation of a boryl moiety to occur at an internal carbon of terminal alkynes in borylstannylation and protoboration. Copper catalysis for C–Sn and C–Si bond-forming processes via distannylation, hydrostannylation and silylstannylation, as well as silver catalysis for a C–B bond-forming reaction, is also described.
Keywords
boron
copper
metalation
silicon
tin
Descriptions
This work was financially supported by Research for Promoting Technological Seeds from the Japan Science and Technology Agency (JST), the Electric Technology Research Foundation of Chugoku, The Mazda Foundation, the Furukawa Technology Promotion Foundation, and the SEI Group CSR Foundation.
Language
eng
Resource Type journal article
Publisher
Wiley
Date of Issued 2016-01-20
Rights
© 2016 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. This is an open access article under the terms of the Creative Commons Attribution-NonCommercial License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
Publish Type Version of Record
Access Rights open access
Source Identifier
[ISSN] 1527-8999
[ISSN] 1528-0691
[DOI] 10.1002/tcr.201500227
[DOI] https://doi.org/10.1002/tcr.201500227