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Volumn 49, Issue 38, 2010, Pages 6840-6843

Mechanistic insights into direct amide bond formation catalyzed by boronic acids: Halogens as Lewis bases

Author keywords

Amide coupling; Density functional calculations; Hydrogen bonds; Organocatalysis; Sustainable chemistry

Indexed keywords

AMIDE BOND FORMATION; BORONIC ACID; DENSITY-FUNCTIONAL CALCULATIONS; DFT CALCULATION; HALOGEN ATOMS; KINETIC PRODUCT; LEWIS BASIS; ORGANOCATALYSIS; RATE DETERMINING STEP; STEREO-SELECTIVE; SUSTAINABLE CHEMISTRY; TETRAHEDRAL INTERMEDIATES; WATER ELIMINATION;

EID: 77956574761     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201003188     Document Type: Article
Times cited : (113)

References (35)
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    • For full computational details, see the Supporting Information
    • For full computational details, see the Supporting Information.
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    • To avoid misleading representations of electron densities (e.g. negatively charged boron atoms), formal charges have been intentionally omitted from all the drawings in this article
    • To avoid misleading representations of electron densities (e.g. negatively charged boron atoms), formal charges have been intentionally omitted from all the drawings in this article.
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    • One referee suggested that the reactions with ortho-halophenylboronic acids as catalysts might proceed via formation of an acyl-halonium intermediate. This hypothesis has been explored computationally for catalyst 4d and the formation of such an intermediate was found to be energetically prohibitive
    • One referee suggested that the reactions with ortho-halophenylboronic acids as catalysts might proceed via formation of an acyl-halonium intermediate. This hypothesis has been explored computationally for catalyst 4d and the formation of such an intermediate was found to be energetically prohibitive.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.