Abstract
An alternative method for the synthesis of 2-heteroaryl or alkynyl benzo[b]thiophene or furan derivatives via direct palladium-catalyzed cross-coupling of 2-benzo[b]thiophene or furan aluminum with heteroaryl or alkynyl bromides, respectively, has been successfully developed. This case is remarkable as the same catalytic system could simultaneously produce either 2-substituted benzo[ b]thiophene or furan derivatives.
Graphical Abstract
[http://dx.doi.org/10.1021/cr100380z] [PMID: 22111507]
[http://dx.doi.org/10.1021/acs.jmedchem.6b01685] [PMID: 28128956]
[http://dx.doi.org/10.1021/jacs.9b10450] [PMID: 32293879]
[http://dx.doi.org/10.1039/c3np70014c] [PMID: 23719995]
[http://dx.doi.org/10.1016/j.bmcl.2009.03.069] [PMID: 19345581]
[http://dx.doi.org/10.2174/1568026616666160927155515] [PMID: 27697050]
[http://dx.doi.org/10.1016/j.bmc.2005.05.009] [PMID: 15964760]
[http://dx.doi.org/10.1039/c3md00130j] [PMID: 23956835]
[http://dx.doi.org/10.1016/j.ejmech.2012.02.021] [PMID: 22405286]
[http://dx.doi.org/10.1111/j.1742-1241.2007.01320.x] [PMID: 17394438]
[http://dx.doi.org/10.1016/j.cbpa.2010.02.018] [PMID: 20303320]
[http://dx.doi.org/10.1002/hlca.200900014]
[http://dx.doi.org/10.1021/jo802736e] [PMID: 19209918]
[http://dx.doi.org/10.1021/ol8029752] [PMID: 19199490]
[http://dx.doi.org/10.1039/c2ob26120k] [PMID: 22878622]
[http://dx.doi.org/10.1039/b212257j] [PMID: 15042150]
[http://dx.doi.org/10.1021/jm2000773] [PMID: 21469694]
[http://dx.doi.org/10.1039/C5OB01905B] [PMID: 26600050]
[http://dx.doi.org/10.1002/anie.200502920] [PMID: 16385605]
[http://dx.doi.org/10.1002/ejoc.202001465]
[http://dx.doi.org/10.1016/j.cclet.2020.02.040]
[http://dx.doi.org/10.1021/jo201081v] [PMID: 21812478]
[http://dx.doi.org/10.1021/acs.joc.0c01516] [PMID: 32940466]
[http://dx.doi.org/10.1021/cr100214d] [PMID: 21425870]
[http://dx.doi.org/10.1039/C6OB00219F] [PMID: 26892101]
[http://dx.doi.org/10.1021/ol302517n] [PMID: 23039199]
[http://dx.doi.org/10.1002/adsc.201501136]
[http://dx.doi.org/10.1039/C6OB02461K] [PMID: 27935619]
[http://dx.doi.org/10.1021/jo101433g] [PMID: 20857989]
[http://dx.doi.org/10.1021/jacs.8b05361] [PMID: 29983049]
[http://dx.doi.org/10.1021/jacs.5b07304] [PMID: 26312441]
[http://dx.doi.org/10.1021/acscentsci.7b00122] [PMID: 28573211]
[http://dx.doi.org/10.1021/acs.joc.6b01060] [PMID: 27362460]
[http://dx.doi.org/10.1039/C8RA03882A] [PMID: 35542491]
[http://dx.doi.org/10.1039/C4CC00815D] [PMID: 24770847]
[http://dx.doi.org/10.1039/C4QO00338A]
[http://dx.doi.org/10.1021/acs.orglett.6b01352] [PMID: 27301433]
[http://dx.doi.org/10.1002/cctc.201601667]
[http://dx.doi.org/10.1021/acs.orglett.6b02857] [PMID: 27754687]
[http://dx.doi.org/10.1002/chem.201702614] [PMID: 28736879]
[http://dx.doi.org/10.1055/s-0037-1610650]
[http://dx.doi.org/10.1016/j.cattod.2018.04.036]
[http://dx.doi.org/10.2174/1385272822666180704143509]
[http://dx.doi.org/10.6023/cjoc201709041]
[http://dx.doi.org/10.1016/j.cclet.2019.02.028]
[http://dx.doi.org/10.2174/1570193]
[http://dx.doi.org/10.6023/cjoc202009029]
[http://dx.doi.org/10.1016/j.tet.2022.132740]
[http://dx.doi.org/10.1021/ol201970m] [PMID: 21882814]
[http://dx.doi.org/10.1021/ol100816g] [PMID: 20420378]
[http://dx.doi.org/10.1016/j.tet.2010.03.055]
[http://dx.doi.org/10.1021/jo0201575] [PMID: 12375989]
[http://dx.doi.org/10.1021/ol102123u] [PMID: 20873816]
[http://dx.doi.org/10.1021/acs.joc.8b00829] [PMID: 29890829]