20143-53-7Relevant articles and documents
Nickel-Catalyzed Intramolecular Nucleophilic Addition of Aryl Halides to Aryl Ketones for the Synthesis of Benzofuran Derivatives
Zhu, Xiao-Rui,Deng, Chen-Liang
supporting information, p. 1842 - 1848 (2021/02/09)
A nickel-catalyzed intramolecular nucleophilic addition reaction of aryl halides to aryl ketones for the formation of benzofuran derivatives has been developed. A number of substrates bearing electron-donating or electron-withdrawing groups were subjected to the standard reaction conditions, giving the corresponding products in moderate to good yields.
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
supporting information, 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.
Total synthesis of protosappanin A and its derivatives via palladium catalyzed ortho C-H activation/C-C cyclization under microwave irradiation
Liu, Jiaqi,Zhou, Xuan,Wang, Chenglong,Fu, Wanyong,Chu, Wenyi,Sun, Zhizhong
, p. 5152 - 5155 (2016/05/02)
A total synthesis method for protosappanin A, which is a complex natural product with many biological activities, was developed with 6 linear steps. Dibenzo[b,d]oxepinones as the key intermediates of the synthetic route were prepared by a palladium-catalyzed ortho C-H activation/C-C cyclization under microwave irradiation. 25 derivatives of protosappanin A were obtained.
Simple N-Heterocyclic Carbenes as Ligands in Ullmann-Type Ether and Thioether Formations
Wu, Jiang-Ping,Saha, Anjan K.,Haddad, Nizar,Busacca, Carl A.,Lorenz, Jon C.,Lee, Heewon,Senanayake, Chris H.
supporting information, p. 1924 - 1928 (2016/07/06)
A simple N-heterocyclic carbene (NHC) derived from 1-methyl-3-ethylimidazolium tetrafluoroborate was found to be an efficient ligand for a range of copper-catalyzed cross-coupling reactions, leading to the formation of aromatic ethers and thioethers. (Figure presented.) .
Palladium(0)-catalyzed single and double isonitrile insertion: A facile synthesis of benzofurans, indoles, and isatins
Senadi, Gopal Chandru,Hu, Wan-Ping,Boominathan, Siva Senthil Kumar,Wang, Jeh-Jeng
supporting information, p. 998 - 1003 (2015/02/05)
A palladium(0)-catalyzed cascade process consisting of isonitrile insertion and ?±-Csp3-H cross-coupling can be achieved for the synthesis of benzofurans and indoles. The construction of isatins by a Pd-catalyzed cascade reaction incorporating double isonitrile insertion, amination, and hydrolysis has also been achieved. The key features of this work include diverse heterocycle synthesis, phosphine-ligand-free reaction conditions, a one-pot procedure, simple and commercially available starting materials, broad functional-group compatibility, and moderate to good reaction yields.
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.
Phase-transfer-catalyzed intramolecular cyclization of ortho-alkynyl phenyl ether derivatives for synthesis of 2,3-disubstituted benzo[b]furans
Hu, Jie,Wu, Lu-Yong,Wang, Xiang-Chuan,Hu, Yuan-Yuan,Niu, Yan-Ning,Liu, Xue-Yuan,Yang, Shangdong,Lianga, Yong-Min
supporting information; experimental part, p. 351 - 356 (2010/04/28)
A variety of substituted benzo[b]furans are readily prepared in good to excellent yields under the mild reaction conditions from o-(1-alkyn-ylphenoxy)- 1-phenylethanone under phase-transfer catalysis (PTC). This methodology accommodates simple experimenta
Iron-catalyzed annulations of 2-(2-alkynyl)phenoxy)-1-arylethanones leading to substituted naphthalen-1-ols
Wang, Zhi-Qiang,Liang, Yun,Lei, Yong,Zhou, Ming-Bo,Li, Jin-Heng
supporting information; scheme or table, p. 5242 - 5244 (2010/01/31)
A novel intramolecular annulation of 1-(2-alkynylphenoxy)propan-2-ones catalyzed by iron, an economical and environmentally-benign transition metal, has been developed; this new atom-economical route includes dual C-H functionalizations to construct the n
Highly regio- and stereoselective synthesis of indene and benzo[b]furan derivatives via a Pd-catalyzed carboannulation of propargyl carbonates with nucleophiles
Bi, Hai-Peng,Guo, Li-Na,Gou, Fa-Rong,Duan, Xin-Hua,Liu, Xue-Yuan,Liang, Yong-Min
, p. 4713 - 4716 (2008/09/21)
(Chemical Equation Presented) A new and efficient synthesis of indene and benzo[b]furan derivatives has been achieved via Pd-catalyzed carboannulation of propargyl carbonates with nucleophiles in good to excellent yields with high regio- and stereoselecti
Palladium(II)-catalyzed intramolecular addition of arylboronic acids to ketones
Liu, Guixia,Lu, Xiyan
, p. 7324 - 7330 (2008/12/20)
A palladium(II)-catalyzed intramolecular addition of arylboronic acids to ketones was developed. Compared to Pd(OAc)2 catalysis system, cationic palladium complex with dppp as the ligand has higher catalytic activity and efficiency for wider sc
