
TY  - JOUR
A1  - Brimble, Margaret A. 
A1  - Issa, Fatiah 
T1  - Reaction of Bromonaphthofurans with Bis(pinacolato)diboron.
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 2000
VL  - 52
IS  - 11
SP  - 1021
EP  - 1028
KW  - 
UR  - https://doi.org/10.1071/CH99073 
N2  - The synthesis of a dimeric pyranonaphthoquinone (8) was investigated focusing on a late-stage biaryl coupling of suitably functionalized bromonaphthofurans by using Suzuki&#8211;Miyaura methodology. Bromonaphthofuran (16) underwent reaction with bis(pinacolato)diboron in the presence of PdCl2(dppf) to afford boronate ester (21) and furonaphthofuran (22). &#8216;In situ&#8217;coupling of the boronate ester (21) with aryl bromide (16) to the desired dimer (11) was not realized. Bromonaphthofuran (17), prepared by Diels&#8211;Alder/retro-Claisen reaction of bromonaphthoquinone (24) with diene (25), underwent Suzuki&#8211;Miyaura coupling to naphthofuran (27) and boronate ester (28). Numerous attempts to alter the reaction conditions to effect homocoupling of bromide (17) to biaryl (19) were unsuccessful. Bromopyranonaphthoquinone (18) prepared by oxidative rearrangement of (17) failed to undergo Suzuki&#8211;Miyaura coupling. 
ER  -

