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Volumn 52, Issue 17, 2013, Pages 4613-4617

Recyclable mitsunobu reagents: Catalytic mitsunobu reactions with an iron catalyst and atmospheric oxygen

Author keywords

alcohols; iron catalysis; Mitsunobu reaction; oxygen; synthetic methods

Indexed keywords

AEROBIC OXIDATIONS; ATMOSPHERIC OXYGEN; CATALYTIC AMOUNTS; IRON CATALYSIS; IRON CATALYST; MITSUNOBU REACTIONS; SYNTHETIC METHODS; TRIPHENYL PHOSPHINES;

EID: 84876474464     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201300153     Document Type: Article
Times cited : (89)

References (46)
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    • We have reported condensation reactions between alcohols and carboxylic acids using triphenylphosphine and atmospheric oxygen in the presence of a catalytic amount of Fe(Pc). The stereochemistry of esters obtained from chiral secondary alcohols was absolutely retained in this reaction, see:, This esterification could compete with the present catalytic Mitsunobu reaction and decrease inversion products in some cases
    • We have reported condensation reactions between alcohols and carboxylic acids using triphenylphosphine and atmospheric oxygen in the presence of a catalytic amount of Fe(Pc). The stereochemistry of esters obtained from chiral secondary alcohols was absolutely retained in this reaction, see:, T. Taniguchi, D. Hirose, H. Ishibashi, ACS Catal. 2011, 1, 1469-1474. This esterification could compete with the present catalytic Mitsunobu reaction and decrease inversion products in some cases.
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    • Taniguchi, T.1    Hirose, D.2    Ishibashi, H.3
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    • Although we never detected peroxides from THF in the present reaction, attention should be given to the possibility of an explosion when a combination of THF and air is used. CPME is a good substitute for THF because the corresponding peroxide is hardly formed under air, see
    • Although we never detected peroxides from THF in the present reaction, attention should be given to the possibility of an explosion when a combination of THF and air is used. CPME is a good substitute for THF because the corresponding peroxide is hardly formed under air, see:, K. Watanabe, N. Yamagiwa, Y. Torisawa, Org. Process Res. Dev. 2007, 11, 251-258.
    • (2007) Org. Process Res. Dev. , vol.11 , pp. 251-258
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.