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For recent reviews of asymmetric catalytic C-F bond formation using electrophilic and nucleophilic fluorine sources, see
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For examples of allylic fluoride motifs in pharmaceutical or imaging agents, see
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For examples of allylic fluoride motifs in pharmaceutical or imaging agents, see
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20
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For reviews, see
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For an unsuccessful investigation, see
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84891728595
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A computational investigation has been reported that supports the feasibility of allylic C-F bond formation from a π-allyl palladium complex
-
A computational investigation has been reported that supports the feasibility of allylic C-F bond formation from a π-allyl palladium complex
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84891727042
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For a discussion of the relative advantages and disadvantages of nucleophilic and electrophilic fluorine sources, see
-
For a discussion of the relative advantages and disadvantages of nucleophilic and electrophilic fluorine sources, see
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34
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54549103372
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84891728630
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2, and several other transition metal fluorides were found to be ineffective as fluoride sources under catalytic conditions similar to those described in Table 2
-
2, and several other transition metal fluorides were found to be ineffective as fluoride sources under catalytic conditions similar to those described in Table 2.
-
-
-
-
39
-
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84891732353
-
-
Allylic chlorides can be prepared from allylic alcohols in one step. See Supporting Information for details
-
Allylic chlorides can be prepared from allylic alcohols in one step. See Supporting Information for details.
-
-
-
-
40
-
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84891727248
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Togni and Mezzetti have reported a ruthenium complex that promotes Br/F exchange between alkyl, allyl, and benzyl bromides and TlF; see
-
Togni and Mezzetti have reported a ruthenium complex that promotes Br/F exchange between alkyl, allyl, and benzyl bromides and TlF; see
-
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41
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Barthazy, P., Hintermann, L., Stoop, R., Wörle, M., Mezzetti, A., and Togni, A. Helv. Chim. Acta 1999, 82, 2448-2453
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43
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84891731563
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Finkelstein reactions between allylic halides and silver fluoride have been reported. For an example, see
-
Finkelstein reactions between allylic halides and silver fluoride have been reported. For an example, see
-
-
-
-
44
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46149142486
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45
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84891728284
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-
Among the solvents tested, toluene and THF were optimal. Reactions conducted above room temperature or in more polar solvents showed increased background reactivity, presumably due in part to the enhanced solubility of AgF under these conditions
-
Among the solvents tested, toluene and THF were optimal. Reactions conducted above room temperature or in more polar solvents showed increased background reactivity, presumably due in part to the enhanced solubility of AgF under these conditions.
-
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46
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50
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84891729611
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We have found that five- and seven-membered allylic chlorides undergo fluorination with reduced efficiency and enantioselectivity. An acyclic allylic chloride, (E)-6-chloronon-4-ene, also reacted with low enantioselectivity. See Supporting Information for details
-
We have found that five- and seven-membered allylic chlorides undergo fluorination with reduced efficiency and enantioselectivity. An acyclic allylic chloride, (E)-6-chloronon-4-ene, also reacted with low enantioselectivity. See Supporting Information for details.
-
-
-
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51
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84891727118
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Allylic fluorides 2 and 5 are unstable to borosilicate glass in neat form. See
-
Allylic fluorides 2 and 5 are unstable to borosilicate glass in neat form. See
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54
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56
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84891731303
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Allylic fluorinations set up under an inert atmosphere, with rigorous exclusion of air and moisture, proceed with comparable % yield and % ee
-
Allylic fluorinations set up under an inert atmosphere, with rigorous exclusion of air and moisture, proceed with comparable % yield and % ee.
-
-
-
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57
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84891725397
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Oxidative addition of Pd(0) to allylic chlorides with inversion of configuration has been documented. See ref 14
-
Oxidative addition of Pd(0) to allylic chlorides with inversion of configuration has been documented. See ref 14.
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33750620556
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Trost, B. M., Machacek, M. R., and Aponick, A. Acc. Chem. Res. 2006, 39, 747-760
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