Abstract
A tandem system that enabled the synthesis of 2-substituted benzo[b]furans from 2- halophenols and aryl acetylenes catalyzed by Ni/5-bromo-2,2’-dipyridine was explored. The protocol was found effective for one-pot cascade coupling cyclization reaction producing benzo[b]furan compounds, and heteroaryl substrates were observed to be compatible for this system as well, giving corresponding products in 20-70% yields.
Keywords: NiCl2, 2-substituted benzo[b]furan, tandem reaction, 2-halophenol, alkyne, sonogashira reaction.
Graphical Abstract
[http://dx.doi.org/10.1016/bs.aihch.2015.08.003]
[http://dx.doi.org/10.2174/157017912802651393]
[http://dx.doi.org/10.1021/acs.jnatprod.7b00791] [PMID: 29394065]
[http://dx.doi.org/10.2174/1570193X16666190710122912]
[http://dx.doi.org/10.1021/jacs.5b08039] [PMID: 26334367]
[http://dx.doi.org/10.3390/catal8040125]
[http://dx.doi.org/10.2174/1570178615666180815124425]
[http://dx.doi.org/10.6023/cjoc201807040]
[http://dx.doi.org/10.1039/C3CC47323F] [PMID: 24770847]
[http://dx.doi.org/10.1021/acsomega.8b02120] [PMID: 31458168]
[http://dx.doi.org/10.2174/1570178614666170321125853]
[http://dx.doi.org/10.1016/j.tetlet.2003.09.080]
[http://dx.doi.org/10.1002/slct.201803292]
[http://dx.doi.org/10.1007/s12039-018-1449-9]
[http://dx.doi.org/10.1002/cctc.201601667]
[http://dx.doi.org/10.1016/j.tetlet.2010.03.072]
[http://dx.doi.org/10.1016/j.tetlet.2018.11.076]
[http://dx.doi.org/10.1002/adsc.201000730]
[http://dx.doi.org/10.1016/j.tetlet.2016.12.076]
[http://dx.doi.org/10.1002/slct.201900519]
[http://dx.doi.org/10.1039/C7OB00009J] [PMID: 28203674]
[http://dx.doi.org/10.1021/jo401503t] [PMID: 23952238]
[http://dx.doi.org/10.1039/C7CS00216E] [PMID: 28675200]
[http://dx.doi.org/10.1007/s10593-014-1458-7]
[http://dx.doi.org/10.1021/jacs.6b12434] [PMID: 28170243]
[http://dx.doi.org/10.3390/catal9121019]
[http://dx.doi.org/10.1002/anie.201908268]
[http://dx.doi.org/10.1016/j.molstruc.2020.128572]
[http://dx.doi.org/10.1007/s12039-011-0137-9]