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Volumn 132, Issue 49, 2010, Pages 17402-17404

Palladium-catalyzed asymmetric synthesis of allylic fluorides

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC CHLORIDE; ASYMMETRIC SYNTHESIS; BISPHOSPHINE; C-F BONDS; ENANTIOSELECTIVE; NUCLEOPHILIC FLUORINATION;

EID: 78650123512     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja109120n     Document Type: Article
Times cited : (166)

References (59)
  • 1
    • 84891726862 scopus 로고    scopus 로고
    • For a recent review, see
    • For a recent review, see
  • 13
    • 84891729690 scopus 로고    scopus 로고
    • For recent reviews of asymmetric catalytic C-F bond formation using electrophilic and nucleophilic fluorine sources, see
    • For recent reviews of asymmetric catalytic C-F bond formation using electrophilic and nucleophilic fluorine sources, see
  • 16
    • 84891727696 scopus 로고    scopus 로고
    • For a review, see
    • For a review, see
  • 18
    • 84891729270 scopus 로고    scopus 로고
    • For examples of allylic fluoride motifs in pharmaceutical or imaging agents, see
    • For examples of allylic fluoride motifs in pharmaceutical or imaging agents, see
  • 25
    • 84891726082 scopus 로고    scopus 로고
    • For reviews, see
    • For reviews, see
  • 29
    • 84891729168 scopus 로고    scopus 로고
    • For an unsuccessful investigation, see
    • For an unsuccessful investigation, see
  • 31
    • 84891728595 scopus 로고    scopus 로고
    • 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
  • 33
    • 84891727042 scopus 로고    scopus 로고
    • 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
  • 38
    • 84891728630 scopus 로고    scopus 로고
    • 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
    • 84891732353 scopus 로고    scopus 로고
    • 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
    • 84891727248 scopus 로고    scopus 로고
    • 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
  • 43
    • 84891731563 scopus 로고    scopus 로고
    • 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
  • 45
    • 84891728284 scopus 로고    scopus 로고
    • 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.
  • 50
    • 84891729611 scopus 로고    scopus 로고
    • 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.
  • 51
    • 84891727118 scopus 로고    scopus 로고
    • 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
  • 56
    • 84891731303 scopus 로고    scopus 로고
    • 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.
  • 57
    • 84891725397 scopus 로고    scopus 로고
    • 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.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.