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Volumn 53, Issue 48, 2014, Pages 13278-13281

B(C6F5)3-catalyzed hydrogenation of oxime ethers without cleavage of the N-O bond

Author keywords

Boron; Homogeneous catalysis; Hydrogenation; Lewis acids; Reduction

Indexed keywords

AMINES; BORON; CATALYSIS; ETHERS; REACTION KINETICS; REDUCTION;

EID: 84915758907     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201407324     Document Type: Article
Times cited : (53)

References (58)
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    • We observed no conversion when employing tris(5,6,7,8-tetrafluoronaphthalen- 2-yl)borane as the catalyst in the hydrogenation of 1c, although we recently showed that this borane is almost as Lewis acidic as B(C6F5)3 and performs equally well in catalytic transformations involving Si-H bond activation: J. Mohr,M. Durmaz, E. Irran, M. Oestreich, Organometallics 2014, 33, 1108-1111.
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    • We assume that heterolytic splitting of the shorter H-H bond is prevented by steric repulsion of the naphthyl groups of this borane and the substrate. Indeed, the reaction with Stephanes borane B(2,3,5,6-F4C6H)3, which is comparably Lewis acidic but smaller, showed full conversion under the same reaction conditions. For the preparation of B(2,3,5,6-F4C6H)3, see:M. Ullrich, A. J. Lough,D. W. Stephan, J. Am. Chem. Soc. 2009, 131, 52-53.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.