908119-67-5Relevant articles and documents
Halogen-metal exchange/cyclization of iodoketones: A direct synthesis of 3-arylbenzofurans
Kraus, George A.,Schroeder, Jacob D.
, p. 2504 - 2506 (2005)
The first synthesis of benzofuran 2 was achieved in 17% overall yield in seven steps. The key step was a halogen-metal exchange/cyclization reaction. Several examples of this reaction were reported. Georg Thieme Verlag Stuttgart.
Nickel-Catalyzed Asymmetric Addition of Aromatic Halides to Ketones: Highly Enantioselective Synthesis of Chiral 2,3-Dihydrobenzofurans Containing a Tertiary Alcohol
Li, Ying,Li, Wendian,Tian, Jiangyan,Huang, Guozheng,Lv, Hui
, p. 5353 - 5357 (2020/07/14)
A highly enantioselective and straightforward synthetic procedure to chiral 3-hydroxy-2,3-dihydrobenzofurans has been developed by nickel/bisoxazoline-catalyzed intramolecular asymmetric addition of aryl halides to unactivated ketones, giving 2,3-dihydrobenzofurans with a chiral tertiary alcohol at the C-3 position in good yields and excellent enantioselectivities (up to 92percent yield and 98percent ee). The gram-scale reaction also proceeded smoothly without a loss of yield and enantioselectivity.
tert-BuOK-mediated carbanion-yne intramolecular cyclization: Synthesis of 2-substituted 3-benzylbenzofurans
Chen, Po-Yuan,Wang, Tzu-Pin,Huang, Keng-Shiang,Kao, Chai-Lin,Tsai, Jui-Chi,Wang, Eng-Chi
experimental part, p. 9291 - 9297 (2011/12/02)
A mild, efficient, and regioselective carbanion-yne intramolecular cyclization mediated by t-BuOK for the synthesis of 2-substituted 3-benzylbenzofurans is developed. It was started from o-iodophenol (1), based on O-alkylation, and the Sonogashira reaction in sequence to produce 2-(2-phenylethynylphenoxy)-1-arylalkanones (5). An intramolecular carbanion-yne 5-exo-dig cyclization reaction of 5, which was mediated by t-BuOK, yielded title benzofurans in good yields.