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4,5,6,7-Tetrachlorobenzo[d][1,3,2]dioxaborol- 2-ol as an effective catalyst for the amide condensation of sterically demanding carboxylic acids.
MedLine Citation:
PMID:  16562909     Owner:  NLM     Status:  PubMed-not-MEDLINE    
[reaction: see text] 4,5,6,7-Tetrachlorobenzo[d][1,3,2]dioxaborole (4a) and 4,5,6,7-tetrachlorobenzo[d][1,3,2]dioxaborol-2-ol (4b) are effective catalysts for the dehydrative amide condensation between an equimolar mixture of carboxylic acids and amines. In particular, these catalysts are greatly superior to 3,5-bis(trifluoromethyl)phenylboronic acid (1) for the amide condensation of sterically demanding carboxylic acids. In contrast, 4c, which is prepared from a 1:2 molar mixture of B(OH)(3) and tetrachlorocatechol, is effective as a Lewis acid-assisted Brønsted acid (LBA) catalyst for Ritter reaction.
Toshikatsu Maki; Kazuaki Ishihara; Hisashi Yamamoto
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Organic letters     Volume:  8     ISSN:  1523-7060     ISO Abbreviation:  Org. Lett.     Publication Date:  2006 Mar 
Date Detail:
Created Date:  2006-03-27     Completed Date:  2006-12-21     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1431-4     Citation Subset:  -    
Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan.
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