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Literature DB >> 15281767

A hierarchy of aryloxide deprotection by boron tribromide.

Sreenivas Punna¹, Stéphane Meunier, M G Finn.

Abstract

Aryl propargyl ethers and esters are cleaved selectively in the presence of aryl methyl ethers and esters by boron tribromide in dichloromethane. Under the same conditions, allyl ethers undergo very rapid Claisen rearrangement, and benzyl ethers are also cleaved more rapidly than propargyl. A mechanism involving intramolecular delivery of bromide to the propargyl terminus is proposed. [reaction: see text]

Entities: Chemical

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Year: 2004 PMID： 15281767 DOI： 10.1021/ol0489898

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

9 in total

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Authors: Patrick T Weiser; Ching-Yi Chang; Donald P McDonnell; Robert N Hanson
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A hierarchy of aryloxide deprotection by boron tribromide.

1. Application of a new phosphorus-free palladium heterogeneous nanocatalyst supported on modified MWCNT the highly selective and efficient cleavage of propargyl, allyl, and benzyl phenol ethers under mild conditions.

2. Cycloaddition of Arynes and Cyclic Enol Ethers as a Platform for Access to Stereochemically Defined 1,2-Disubstituted Benzocyclobutenes.

3. An unusual reactivity of BBr(3): Accessing tetrahydroisoquinoline units from N-phenethylimides.

4. 4,4'-Unsymmetrically substituted 3,3'-biphenyl alpha helical proteomimetics as potential coactivator binding inhibitors.

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6. Direct Conversion of Aldehydes and Ketones to Allylic Halides by a NbX(5-)[3,3] Rearrangement.

7. Ether Cleavage Re-Investigated: Elucidating the Mechanism of BBr₃-Facilitated Demethylation of Aryl Methyl Ethers.

8. Designing Light-Activated Charge-Separating Proteins with a Naphthoquinone Amino Acid.

9. Derivatives of a PARP Inhibitor TIQ-A through the Synthesis of 8-Alkoxythieno[2,3-c]isoquinolin-5(4H)-ones.