Journal
COMMUNICATIONS CHEMISTRY
Volume 4, Issue 1, Pages -Publisher
NATURE RESEARCH
DOI: 10.1038/s42004-021-00478-2
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Funding
- Anhui Provincial Natural Science Foundation [1808085MB41]
- National Natural Science Foundation of China [21772001]
- Cultivation Project for University Outstanding Talents of Anhui Province (2019)
- Research Grants Council of Hong Kong (GRF) [14304519-19P]
- CUHK Direct Fund [4442353]
- Guangdong Basic and Applied Basic Research Foundation [2019A1515011357]
- Innovation and Technology Commission (HKSAR, China)
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The study presents a method for accessing dibenzofurans with diverse substitution patterns through a double 1,4-conjugate addition/intramolecular annulation cascade reaction, which allows for efficient manipulation of substituents on the core structure.
Existing synthetic routes for accessing dibenzofuran core have intrinsic regioselectivity, limiting the substitution patterns available in heteropolycyclic arene products. Here we report a double 1,4-conjugate addition/intramolecular annulation cascade reaction between propargylamines and two equivalents of imidazolium methylides that allows efficient access of structurally versatile dibenzofurans. This transition metal-free protocol proceeds smoothly under bench-top air atmosphere and offers easy manipulation of substituents on the dibenzofuran core, and also provides good-to-excellent product yields with good functional group tolerance, particularly the -Br and -Cl groups which are often incompatible with existing metal-catalyzed C-C and/or C-O bond ring-forming processes. It is worth noting that ladder-type -systems with all-arene quarternary carbon structure can be straightforwardly generated upon simple late-stage functionalization. Existing routes to dibenzofurans have intrinsic regioselectivity, limiting the substitution patterns available in the products. Here a double 1,4-conjugate addition-annulation cascade between propargylamines and imidazolium methylides provides direct access to dibenzofurans with a complementary substitution pattern.
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