Organic Chemistry Portal
Organic Chemistry Highlights

Monday, October 19, 2020
Douglass F. Taber
University of Delaware

Heteroaromatics: The Pritchard/Kimber Synthesis of 11D5(F6)

Martin E. Maier of the Eberhard Karls Universität Tübingen used a gold catalyst to cyclize 1 to the furan 2 (J. Org. Chem. 2020, 85, 8203. DOI: 10.1021/acs.joc.0c00408). Junfeng Zhao of Jiangxi Normal University assembled 5 by combining 3 with 4 (J. Org. Chem. 2020, 85, 3902. DOI: 10.1021/acs.joc.9b03006).

Milos Petkovic and Vladimir Savic of the University of Belgrade observed high diastereocontrol in the cyclization of 6, leading after oxidation to 7 (Eur. J. Org. Chem. 2020, 295. DOI: 10.1002/ejoc.201901554). Qiang Zhu and Shuang Luo of the Guangzhou Institutes of Biomedicine and Health prepared the pyrrole 9 by oxidizing 8 in the presence of benzylamine (Tetrahedron Lett. 2020, 61, 151887. DOI: 10.1016/j.tetlet.2020.151887).

Xianjie Fang of Shanghai Jiao Tong University reduced the bis nitrile 10, leading to the pyridine 11 (Chem. Commun. 2020, 56, 6858. DOI: 10.1039/D0CC02938F). K. C. Kumara Swamy of the University of Hyderabad assembled 14 by combining 12 with 13 (J. Org. Chem. 2020, 85, 4130. DOI: 10.1021/acs.joc.9b03281). Sampak Samanta of the Indian Institute of Technology Indore described a parallel investigation (J. Org. Chem. 2020, 85, 2151. DOI: 10.1021/acs.joc.9b02896). Kai Guo of Nanjing Tech University prepared the pyridine 17 by combining 15 with 16 (J. Org. Chem. 2020, 85, 8157. DOI: 10.1021/acs.joc.0c01081). Kay Severin and Nicolai Cramer of the Ecole Polytechnique Fédérale de Lausanne observed that the dialkyl triazene of 19 survived Ru-mediated combination with 18, to subsequently be converted to the iodide of 20 (J. Am. Chem. Soc. 2019, 141, 10372. DOI: 10.1021/jacs.9b04111).

Yan-Biao Kang of the University of Science and Technology of China and Jiang-Ping Qu, also of Nanjing Technical University combined 21 with 22 to give the indole 23 (Org. Lett. 2020, 22, 4553. DOI: 10.1021/acs.orglett.0c01615). Yong Rok Lee of Yeungnam University devised the oxidative cylization of 24 with 25, leading to 26 (Org. Lett. 2020, 22, 3397. DOI: 10.1021/acs.orglett.0c00877). Antonio C. B. Burtoloso of the Universidade de São Paulo cyclized 27 directly to 28 (J. Org. Chem. 2020, 85, 7433. DOI: 10.1021/acs.joc.0c00833). Ramesh Giri of Pennsylvania State University prepared 31 by combining 29 with two equivalents of fumaronitrile 30 (Org. Lett. 2020, 22, 3268. DOI: 10.1021/acs.orglett.0c01057).

Furan fatty acids, illusrated by 11D5(F6) (35), are important in the human diet. Gareth J. Pritchard and Marc C. Kimber of Loughborough University established a general route to these acids, exemplified by the assembly of 34 by the combination of 32 with 33 (Eur. J. Org. Chem. 2020, 2914. DOI: 10.1002/ejoc.202000234).

D. F. Taber, Org. Chem. Highlights 2020, October 19.