Synthesis of diverse unsymmetric 1,4-adducts via a three-component coupling reaction of malonate derivatives, [60]fullerene and electrophiles/nucleophiles

Abstract

Three-component coupling reaction of malonate derivatives, [60]fullerene, and electrophiles/nucleophiles has been developed as a facile and efficient method to access various 1,4-asymmetric malonate functionalized [60]fullerenes. This methodology features low cost,...

Synthesis of Cs-symmetrical C60 tetra-adducts via reactions of C60Cl6 with CH-acids and enol silyl ester

“…17,18 Recently developed modifications of these approaches include a three-component coupling reaction of malonate derivatives, [60]fullerene, and electrophiles/ nucleophiles. 19 However, these reactions do not allow the selective obtaining of highly functionalized fullerene derivatives, bearing two or more addends without additional techniques, such as utilizing tether-bridged ditopic reagents, coordination cages and metal-organic frameworks. 20 Taking this into account, the reaction of C 60 with silyl esters of enols, reported for the first time by Mikami et al 21 and developed by Nakamura and colleagues (Fig.…”

“…17,18 Recently developed modifications of these approaches include a three-component coupling reaction of malonate derivatives, [60]fullerene, and electrophiles/nucleophiles. 19…”

One‐Pot Synthesis of Diverse 1,4‐[60]Fullerephenols via Three‐Component Umpolung Cascade Coupling of Phenols, C60, and Nucleophiles

“…Although a number of methods have been reported for synthesizing 1,4‐fullerene derivatives, [5e,11] to the best of our knowledge, the facile preparation of diversified 1,4‐(4‐phenol)‐(organo)[60]fullerenes remains very challenging. Recently, the two consecutive inversions of the polarity of C 60 , have been developed as a practical and efficient protocol for the one‐pot synthesis of various 1,4‐(3‐indole)‐(organo)[60]fullerenes [12a–b] and 1,4‐(malonate)‐(organo)‐[60]fullerenes [12c] . This one‐pot umpolung cascade strategy hold tremendous potential for the regiocontrolled synthesis of a large range of novel functionalized fullerenes that are otherwise difficult to synthesize in an efficient and selective manner.…”