A facile 2H-chromene dimerization through an ortho-quinone methide intermediate catalyzed by a sulfonyl derived MIL-101 MOF. (2nd July 2018)

• Record Type: Journal Article
• Authors: Du, Xin; Li, Xiujuan; Tang, Houliang; Wang, Wenyu; Ramella, Daniele; Luan, Yi
• Is Part Of: New journal of chemistry. Volume 42:Number 15(2018)
• Page Start: 12722
• Page End: 12728
• Publication Date: 2018-07-02
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/c8nj01354c
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : An efficient homo-dimerization of 2 H -chromenes was achieved in high yield and diastereoselectivity using a MIL-101–SO3 H MOF catalyst. Abstract : A MIL-101–SO3 H MOF was synthesized using commercially available materials. The as-synthesized MIL-101–SO3 H was characterized by SEM, XRD, FTIR, BET and TGA. An efficient and diastereoselective homo-dimerization of 2 H -chromenes catalysis was achieved using the sulfonyl derived MIL-101 MOF as a catalyst. A benzopyranobenzopyran polycyclic structure was generated in high yield and diastereoselectivity under mild catalytic reaction conditions. Furthermore, a regio-isomer was observed when 2 H -chromene bears different substitution groups, furnishing chromeno[2, 3- b ]chromene dimer in high yield and good diastereoselectivity. A mechanism is proposed with a tandem rearrangement/hetero-Diels–Alder reaction sequence which is supported by evidence. In addition, the acid MIL-101 MOF catalyst can be recycled ten times without compromising the yield and selectivity.