Rhodium(ii)-catalyzed divergent intramolecular tandem cyclization of N- or O-tethered cyclohexa-2,5-dienones with 1-sulfonyl-1,2,3-triazole: synthesis of cyclopropa[cd]indole and benzofuran derivatives

Zhu, Cheng-Zhi1; Wei, Yin1; Shi, Min1,2,3,4

2019-08-21

10.1039/c9qo00714h

Organic Chemistry Frontiers   影响因子和分区

2052-4129

A rhodium(ii)-catalyzed divergent intramolecular tandem cyclization of N- or O-tethered cyclohexa-2,5-dienones with 1-sulfonyl-1,2,3-triazole has been disclosed in this paper. When the connecting atom between the cyclohexa-2,5-dienone unit and the 1-sulfonyl-1,2,3-triazole moiety was a N-sulfonated group, a cyclopropanation of the olefinic unit in the cyclohexa-2,5-dienone moiety could take place, affording cyclopropa[cd]indole derivatives in moderate to good yields. This is the first example of the cyclopropanation of alpha-imino rhodium carbenes with electron-deficient intra-annular olefins. If the connecting linker was an oxygen atom, an oxy-Cope rearrangement could be triggered under similar reaction conditions, giving benzofuran derivatives. The reaction mechanisms have also been proposed along with a synthetic transformation.

SCI ; EI ; IC ; CCR

英语

通讯

Fundamental Research Funds for the Central Universities[222201717003]

Chemistry

Chemistry, Organic

WOS:000484262900007

ROYAL SOC CHEMISTRY

20193307308668

Catalysis ; Polycyclic aromatic hydrocarbons ; Rhodium compounds

Chemical Reactions:802.2 ; Organic Compounds:804.1

Web of Science

1.Chinese Acad Sci, Univ Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem,Ctr Excellence Mo, 345 Lingling Rd, Shanghai 200032, Peoples R China
2.East China Univ Sci & Technol, Key Lab Adv Mat, Sch Chem & Mol Engn, Meilong Rd 130, Shanghai SHANGHAI, Peoples R China
3.East China Univ Sci & Technol, Inst Fine Chem, Sch Chem & Mol Engn, Meilong Rd 130, Shanghai SHANGHAI, Peoples R China
4.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Shenzhen 518000, Guangdong, Peoples R China

Zhu, Cheng-Zhi,Wei, Yin,Shi, Min. Rhodium(ii)-catalyzed divergent intramolecular tandem cyclization of N- or O-tethered cyclohexa-2,5-dienones with 1-sulfonyl-1,2,3-triazole: synthesis of cyclopropa[cd]indole and benzofuran derivatives[J]. Organic Chemistry Frontiers,2019,6(16):2884-2891.

Zhu, Cheng-Zhi,Wei, Yin,&Shi, Min.(2019).Rhodium(ii)-catalyzed divergent intramolecular tandem cyclization of N- or O-tethered cyclohexa-2,5-dienones with 1-sulfonyl-1,2,3-triazole: synthesis of cyclopropa[cd]indole and benzofuran derivatives.Organic Chemistry Frontiers,6(16),2884-2891.

Zhu, Cheng-Zhi,et al."Rhodium(ii)-catalyzed divergent intramolecular tandem cyclization of N- or O-tethered cyclohexa-2,5-dienones with 1-sulfonyl-1,2,3-triazole: synthesis of cyclopropa[cd]indole and benzofuran derivatives".Organic Chemistry Frontiers 6.16(2019):2884-2891.