PMID- 37340217
OWN - NLM
STAT- PubMed-not-MEDLINE
LR  - 20230919
IS  - 1474-9092 (Electronic)
IS  - 1474-905X (Linking)
VI  - 22
IP  - 10
DP  - 2023 Oct
TI  - Visible-light promoted photoredox catalysis in flow: addition of biologically 
      important alpha‑amino radicals to michael acceptors.
PG  - 2259-2270
LID - 10.1007/s43630-023-00448-8 [doi]
AB  - Visible light promoted photoredox catalyzed formation of alpha-amino radicals from 
      cyclic tertiary amine compounds and their subsequent addition to Michael 
      acceptors performed in flow conditions allowed access to a wide range of 
      functionalized N-aryl-substituted tetrahydroisoquinolines (THIQs) and 
      N-aryl-substituted tetrahydro-beta-carbolines (THBCs). Visible light in conjunction 
      with Ru(bpy)(3)Cl(2) photocatalyst allowed the formation and high reactivities of 
      alpha-amino radicals in flow conditions at room temperature. These reactions gave 
      valuable products with high efficiencies; some previously unavailable reaction 
      pathways photo or thermal reaction conditions; i.e. direct synthesis of 
      1-substituted (THBCs) via alpha-amino radical path were successfully realized in 
      flow. The use of custom-made FEP tube microreactor proved to be the key to 
      succesfull alpha-amino-radical formation and overall reaction performance in flow. 
      Three types of light transparent custom-made microfluidic devices were tested, 
      among them glass/silicon and FEP type reactor showed very good results in the 
      conversion of tested compounds. Plausible reaction mechanism is proposed in 
      accordance with known principles of photo activation of tertiary amines. Visible 
      light promoted C(sp3)-H functionalization of N-aryl-protected 
      tetrahydroisoquinolines and N-aryl-protected tetrahydro-beta-carbolines in microflow 
      conditions via a-amino radical pathway with various coupling partners in 
      excellent yields and efficiencies.
CI  - (c) 2023. The Author(s), under exclusive licence to European Photochemistry 
      Association, European Society for Photobiology.
FAU - Filipovic, Ana
AU  - Filipovic A
AD  - Institute of Chemistry, Technology and Metallurgy, University of Belgrade, 
      National Institute of the Republic of Serbia, Njegoseva 12, 11000, Belgrade, 
      Republic of Serbia.
FAU - Dzambaski, Zdravko
AU  - Dzambaski Z
AD  - Institute of Chemistry, Technology and Metallurgy, University of Belgrade, 
      National Institute of the Republic of Serbia, Njegoseva 12, 11000, Belgrade, 
      Republic of Serbia.
FAU - Bondzic, Aleksandra M
AU  - Bondzic AM
AD  - Vinca Institute of Nuclear Sciences, National Institute of the Republic of 
      Serbia, University of Belgrade, P.O. Box 522, 11000, Belgrade, Serbia.
FAU - Bondzic, Bojan P
AU  - Bondzic BP
AUID- ORCID: 0000-0002-8249-6091
AD  - Institute of Chemistry, Technology and Metallurgy, University of Belgrade, 
      National Institute of the Republic of Serbia, Njegoseva 12, 11000, Belgrade, 
      Republic of Serbia. bojan.bondzic@ihtm.bg.ac.rs.
LA  - eng
GR  - 451-03-47/2023-01/200026/Ministarstvo Prosvete, Nauke i Tehnoloskog Razvoja/
PT  - Journal Article
DEP - 20230621
PL  - England
TA  - Photochem Photobiol Sci
JT  - Photochemical & photobiological sciences : Official journal of the European 
      Photochemistry Association and the European Society for Photobiology
JID - 101124451
SB  - IM
OTO - NOTNLM
OT  - Flow chemistry
OT  - Microfluidic devices
OT  - Photoredox catalysis
OT  - Tertahydroisoquinolines
OT  - Tetrahydro-beta-carbolines
OT  - alpha -amino radicals
EDAT- 2023/06/21 01:07
MHDA- 2023/06/21 01:08
CRDT- 2023/06/20 23:30
PHST- 2023/05/22 00:00 [received]
PHST- 2023/06/08 00:00 [accepted]
PHST- 2023/06/21 01:08 [medline]
PHST- 2023/06/21 01:07 [pubmed]
PHST- 2023/06/20 23:30 [entrez]
AID - 10.1007/s43630-023-00448-8 [pii]
AID - 10.1007/s43630-023-00448-8 [doi]
PST - ppublish
SO  - Photochem Photobiol Sci. 2023 Oct;22(10):2259-2270. doi: 
      10.1007/s43630-023-00448-8. Epub 2023 Jun 21.