Open Access
Open access
Beilstein-Institut
Beilstein Journal of Organic Chemistry
,  том 10 ,  страницы 344-351

Deoxygenative gem-difluoroolefination of carbonyl compounds with (chlorodifluoromethyl)trimethylsilane and triphenylphosphine

Тип публикации: Journal Article
Дата публикации: 2014-02-06
Beilstein-Institut
scimago Q2
wos Q3
БС2
SJR: 0.482
CiteScore: 3.8
Impact factor: 2.1
ISSN: 18605397
Organic Chemistry
Краткое описание

Background: 1,1-Difluoroalkenes cannot only be used as valuable precursors for organic synthesis, but also act as bioisosteres for enzyme inhibitors. Among various methods for their preparation, the carbonyl olefination with difluoromethylene phosphonium ylide represents one of the most straightforward methods.

Results: The combination of (chlorodifluoromethyl)trimethylsilane (TMSCF2Cl) and triphenylphosphine (PPh3) can be used for the synthesis of gem-difluoroolefins from carbonyl compounds. Comparative experiments demonstrate that TMSCF2Cl is superior to (bromodifluoromethyl)trimethylsilane (TMSCF2Br) and (trifluoromethyl)trimethylsilane (TMSCF3) in this reaction.

Conclusion: Similar to many other Wittig-type gem-difluoroolefination reactions in the presence of PPh3, the reaction of TMSCF2Cl with aldehydes and activated ketones is effective.

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Wang F. et al. Deoxygenative gem-difluoroolefination of carbonyl compounds with (chlorodifluoromethyl)trimethylsilane and triphenylphosphine // Beilstein Journal of Organic Chemistry. 2014. Vol. 10. pp. 344-351.
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Wang F., Li L., Ni C., Hu J. Deoxygenative gem-difluoroolefination of carbonyl compounds with (chlorodifluoromethyl)trimethylsilane and triphenylphosphine // Beilstein Journal of Organic Chemistry. 2014. Vol. 10. pp. 344-351.
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TY - JOUR
DO - 10.3762/bjoc.10.32
UR - https://doi.org/10.3762/bjoc.10.32
TI - Deoxygenative gem-difluoroolefination of carbonyl compounds with (chlorodifluoromethyl)trimethylsilane and triphenylphosphine
T2 - Beilstein Journal of Organic Chemistry
AU - Wang, Fei
AU - Li, Lingchun
AU - Ni, Chuanfa
AU - Hu, Jinbo
PY - 2014
DA - 2014/02/06
PB - Beilstein-Institut
SP - 344-351
VL - 10
PMID - 24605155
SN - 1860-5397
ER -
BibTex
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@article{2014_Wang,
author = {Fei Wang and Lingchun Li and Chuanfa Ni and Jinbo Hu},
title = {Deoxygenative gem-difluoroolefination of carbonyl compounds with (chlorodifluoromethyl)trimethylsilane and triphenylphosphine},
journal = {Beilstein Journal of Organic Chemistry},
year = {2014},
volume = {10},
publisher = {Beilstein-Institut},
month = {feb},
url = {https://doi.org/10.3762/bjoc.10.32},
pages = {344--351},
doi = {10.3762/bjoc.10.32}
}