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Tunable and chemoselective syntheses of dihydroisobenzofurans and indanones via rhodium-catalyzed tandem reactions of 2-triazole-benzaldehydes and 2-triazole-alkylaryl ketones.
Org Lett. 2014 Nov 07; 16(21):5588-91.OL

Abstract

Two novel rhodium(II)-catalyzed tandem reactions were developed for the synthesis of dihydroisobenzofuran and indanone derivatives from 2-triazole-benzaldehydes and 2-triazole-alkylaryl ketones. Dihydroisobenzofuran derivatives were obtained in good yields with high regioselectivities when alcohols were used as nuclophiles in these reactions, whereas the replacement of the alcohol with water resulted in the diastereoselective formation of highly functionalized indanone derivatives.

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Authors+Show Affiliations

Shen H
Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School , Shenzhen 518055, China.
Fu J
No affiliation info available
Gong J
No affiliation info available
Yang Z
No affiliation info available

MeSH

BenzaldehydesBenzofuransCatalysisIndansKetonesMolecular StructureRhodiumStereoisomerismTriazoles

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

25327974

Citation

Shen, Hongjuan, et al. "Tunable and Chemoselective Syntheses of Dihydroisobenzofurans and Indanones Via Rhodium-catalyzed Tandem Reactions of 2-triazole-benzaldehydes and 2-triazole-alkylaryl Ketones." Organic Letters, vol. 16, no. 21, 2014, pp. 5588-91.
Shen H, Fu J, Gong J, et al. Tunable and chemoselective syntheses of dihydroisobenzofurans and indanones via rhodium-catalyzed tandem reactions of 2-triazole-benzaldehydes and 2-triazole-alkylaryl ketones. Org Lett. 2014;16(21):5588-91.
Shen, H., Fu, J., Gong, J., & Yang, Z. (2014). Tunable and chemoselective syntheses of dihydroisobenzofurans and indanones via rhodium-catalyzed tandem reactions of 2-triazole-benzaldehydes and 2-triazole-alkylaryl ketones. Organic Letters, 16(21), 5588-91. https://doi.org/10.1021/ol502617m
Shen H, et al. Tunable and Chemoselective Syntheses of Dihydroisobenzofurans and Indanones Via Rhodium-catalyzed Tandem Reactions of 2-triazole-benzaldehydes and 2-triazole-alkylaryl Ketones. Org Lett. 2014 Nov 7;16(21):5588-91. PubMed PMID: 25327974.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Tunable and chemoselective syntheses of dihydroisobenzofurans and indanones via rhodium-catalyzed tandem reactions of 2-triazole-benzaldehydes and 2-triazole-alkylaryl ketones. AU - Shen,Hongjuan, AU - Fu,Junkai, AU - Gong,Jianxian, AU - Yang,Zhen, Y1 - 2014/10/20/ PY - 2014/10/21/entrez PY - 2014/10/21/pubmed PY - 2015/2/6/medline SP - 5588 EP - 91 JF - Organic letters JO - Org Lett VL - 16 IS - 21 N2 - Two novel rhodium(II)-catalyzed tandem reactions were developed for the synthesis of dihydroisobenzofuran and indanone derivatives from 2-triazole-benzaldehydes and 2-triazole-alkylaryl ketones. Dihydroisobenzofuran derivatives were obtained in good yields with high regioselectivities when alcohols were used as nuclophiles in these reactions, whereas the replacement of the alcohol with water resulted in the diastereoselective formation of highly functionalized indanone derivatives. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/25327974/Tunable_and_chemoselective_syntheses_of_dihydroisobenzofurans_and_indanones_via_rhodium_catalyzed_tandem_reactions_of_2_triazole_benzaldehydes_and_2_triazole_alkylaryl_ketones_ DB - PRIME DP - Unbound Medicine ER -