期刊
ACS CATALYSIS
卷 7, 期 6, 页码 4197-4201出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b00716
关键词
substituted naphthalenes; amino-benzocyclobutenes; photocatalysis; annulation; C-C cleavage
资金
- University of Arkansas
- Arkansas Bioscience Institute
- National Institutes of Health (NIH) from the National Institute of General Medical Sciences [P30 GM103450]
- NSF Career Award [CHE-1255539]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1255539] Funding Source: National Science Foundation
We report a visible-light-promoted synthesis of substituted naphthalenes via [4 + 2] annulation of amino-benzocyclobutenes with alkynes. Amino-benzocyclobutenes, which are conveniently synthesized by [2 + 2] cycloaddition of arynes with ketenes followed by reductive amination, undergo regioselective opening of the cyclobutenyl ring to reveal a presumably distonic radical cation upon photooxidation by an excited iridium complex. The distonic radical cation undergoes the annulation with terminal and internal alkynes as well as diynes to afford structurally diverse naphthalenes. The regiochemistry of the annulation follows the pattern displayed in the addition of nucleophilic carbon radicals to alkynes. The aniline group plays a dual role in which it not only directs the initial photooxidation to generate the amine radical cation but also serves as a leaving group to complete aromatization.
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