Document Detail

Rhodium-Catalyzed B-H Activation of 1,2-Azaborines: Synthesis and Characterization of BN Isosteres of Stilbenes.
MedLine Citation:
PMID:  24916200     Owner:  NLM     Status:  Publisher    
The first example of catalytic B-H activation of azaborines leading to a new family of stilbene derivatives through dehydrogenative borylation is reported. Ten 1,2-azaborine-based BN isosteres of stilbenes have been synthesized using this method, including a BN isostere of a biologically active stilbene. It is demonstrated that BN/CC isosterism in the context of stilbenes can lead to significant changes in the observed photophysical properties such as higher quantum yield and a larger Stokes shift. Direct comparative analysis of BN stilbene 3g and its carbonaceous counterpart 6g is consistent with a stronger charge-transfer character of the excited state exhibited by 3g in which the 1,2-azaborine heterocycle serves as a better electron donor than the corresponding arene.
Alec N Brown; Lev N Zakharov; Tanya Mikulas; David A Dixon; Shih-Yuan Liu
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2014-6-11
Journal Detail:
Title:  Organic letters     Volume:  -     ISSN:  1523-7052     ISO Abbreviation:  Org. Lett.     Publication Date:  2014 Jun 
Date Detail:
Created Date:  2014-6-11     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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