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author:

Ye, J. (Ye, J..) [1] | Wu, J. (Wu, J..) [2] | Lv, T. (Lv, T..) [3] | Wu, G. (Wu, G..) [4] | Gao, Y. (Gao, Y..) [5] | Chen, H. (Chen, H..) [6]

Indexed by:

Scopus

Abstract:

The observation of an unexpected oxidative rearrangement coupling reaction led to the development of a novel method for the efficient functionalization of tetrahydro-β-carbolines (THβCs). The treatment of THβCs with photogenerated singlet oxygen ( 1 O 2 ) afforded unstable dioxetanes, which underwent further transformation to form new bonds in the presence of trifluoroacetic acid. This operationally simple protocol exhibits broad functional-group tolerance and is suitable for the late-stage functionalization of complex druglike molecules. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keyword:

oxidative functionalization; rearrangement; singlet oxygen; tetrahydro-β-carbolines; visible light

Community:

  • [ 1 ] [Ye, J.]College of Chemistry, Fuzhou University, Fuzhou, Fujian 350116, China
  • [ 2 ] [Wu, J.]College of Chemistry, Fuzhou University, Fuzhou, Fujian 350116, China
  • [ 3 ] [Lv, T.]College of Chemistry, Fuzhou University, Fuzhou, Fujian 350116, China
  • [ 4 ] [Wu, G.]College of Chemistry, Fuzhou University, Fuzhou, Fujian 350116, China
  • [ 5 ] [Gao, Y.]College of Chemistry, Fuzhou University, Fuzhou, Fujian 350116, China
  • [ 6 ] [Chen, H.]College of Chemistry, Fuzhou University, Fuzhou, Fujian 350116, China

Reprint 's Address:

  • [Chen, H.]College of Chemistry, Fuzhou UniversityChina

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Source :

Angewandte Chemie - International Edition

ISSN: 1433-7851

Year: 2017

Issue: 47

Volume: 56

Page: 14968-14972

1 2 . 1 0 2

JCR@2017

1 6 . 1 0 0

JCR@2023

ESI HC Threshold:226

JCR Journal Grade:1

CAS Journal Grade:2

Cited Count:

WoS CC Cited Count:

SCOPUS Cited Count: 41

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count:

Chinese Cited Count:

30 Days PV: 0

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