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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 2 (J. Org. Chem. 2020, 85, 8203. ). Junfeng Zhao of Jiangxi Normal University assembled 5 by combining 3 with 4 (J. Org. Chem. 2020, 85, 3902. ).

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. ). 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. ).

Xianjie Fang of Shanghai Jiao Tong University reduced the bis nitrile 10, leading to the pyridine 11 (Chem. Commun. 2020, 56, 6858. ). K. C. Kumara Swamy of the University of Hyderabad assembled 14 by combining 12 with 13 (J. Org. Chem. 2020, 85, 4130. ). Sampak Samanta of the Indian Institute of Technology Indore described a parallel investigation (J. Org. Chem. 2020, 85, 2151. ). Kai Guo of Nanjing Tech University prepared the pyridine 17 by combining 15 with 16 (J. Org. Chem. 2020, 85, 8157. ). 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. ).

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. ). Yong Rok Lee of Yeungnam University devised the oxidative cylization of 24 with 25, leading to 26 (Org. Lett. 2020, 22, 3397. ). Antonio C. B. Burtoloso of the Universidade de São Paulo cyclized 27 directly to 28 (J. Org. Chem. 2020, 85, 7433. ). Ramesh Giri of Pennsylvania State University prepared 31 by combining 29 with two equivalents of fumaronitrile 30 (Org. Lett. 2020, 22, 3268. ).

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. ).

D. F. Taber, Org. Chem. Highlights 2020, October 19.
URL: https://www.organic-chemistry.org/Highlights/2020/19October.shtm