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Synthesis of Trifluoromethyl Tetrafluoro‐λ 6 ‐sulfanyl‐Substituted Alkenes, Ketones, and Acids: Polar Hydrophobic Building Blocks
Author(s) -
Ikeda Akari,
Zhong Linbin,
Savoie Paul R.,
von Hahmann Cortney N.,
Zheng Wei,
Welch John T.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701568
Subject(s) - chemistry , sulfanyl , trifluoromethyl , triethylborane , medicinal chemistry , chloride , aldehyde , organic chemistry , stereochemistry , catalysis , alkyl
The trifluoromethyl tetrafluoro‐λ 6 ‐sulfanyl (CF 3 SF 4 ) group is both extraordinarily lipophilic and profoundly electron withdrawing, properties associated with polar hydrophobicity. Utilization of the CF 3 SF 4 group to prepare novel materials or biologically active agents will not be possible without new methods for the synthesis of aliphatic CF 3 SF 4 ‐substituted building blocks. To advance those studies, trichloromethanesulfenyl chloride was conveniently converted to trans ‐trifluoromethyl tetrafluoro‐λ 6 ‐sulfanyl chloride (CF 3 SF 4 Cl) by oxidative chlorofluorination. Triethylborane‐promoted addition reactions of trans ‐CF 3 SF 4 Cl to substituted olefins and alkynes yielded a variety of new materials. Those addition products were subsequently transformed to CF 3 SF 4 ‐substituted carboxylic acids, CF 3 SF 4 ‐substituted ketones, and a CF 3 SF 4 ‐substituted aldehyde.