期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 50, 页码 26327-26331出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202109461
关键词
boron; DFT modeling; fluorination; organic synthesis; rearrangement
资金
- Knut och Alice Wallenbergs Foundation [2018.0066]
- Swedish Research Council [2017-04235]
- Stiftelsen Olle Engkvist Byggmastare [192-0484]
- Swedish Research Council [2017-04235] Funding Source: Swedish Research Council
- Vinnova [2017-04235] Funding Source: Vinnova
The electrophilic fluorination of geminal alkyl substituted vinyl-Bmida derivatives proceeds via a bora-Wagner-Meerwein rearrangement, with the Bmida group having a larger migration aptitude than the alkyl moiety. This rearrangement occurs with a low activation barrier via a bora-cyclopropane shaped transition state according to DFT modelling studies.
The electrophilic fluorination of geminal alkyl substituted vinyl-Bmida derivatives proceeds via bora-Wagner-Meerwein rearrangement. According to DFT modelling studies this rearrangement occurs with a low activation barrier via a bora-cyclopropane shaped TS. The Bmida group has a larger migration aptitude than the alkyl moiety in the Wagner-Meerwein rearrangement of the presented electrophilic fluorination reactions.
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