Beilstein J. Org. Chem.2016,12, 2065–2076, doi:10.3762/bjoc.12.195
: bromobenzofuran coupling; cross-coupling; palladium; regio-selective; triarylbismuth; Introduction
The benzofuran scaffold is present in various biologically active molecules [1][2][3][4][5][6][7][8], natural products [9][10][11][12][13][14][15] and also part of various functional materials [16]. Importantly
bromobenzofurans with triarylbismuth reagents under palladium coupling conditions.
Results and Discussion
This study was initiated with 2,3-dibromobenzofuran for the investigation of the regio-selective coupling using a triarylbismuth reagent in substoichiometric amounts under Pd-catalyzed conditions (Table 1). A
-dibromobenzofuran (1.1) and 1 equiv of bismuth reagent gave 86% yield (Table 1, entry 10). A few control reactions without base or palladium catalyst showed inferior or no cross-coupling reactivity (Table 1, entries 11 and 12). This investigation results that the desired regio-selective cross-coupling reactivity
Beilstein J. Org. Chem.2016,12, 1765–1771, doi:10.3762/bjoc.12.165
-glucose derived alcohol 3 in 13 steps and 14% overall yield. Thus, the Sharpless asymmetric epoxidation of allyl alcohol 7 followed by trimethyl borate mediated regio-selective oxirane ring opening with azide, afforded azido diol 10. The acid-catalyzed 1,2-acetonide ring opening in 10 concomitantly led to