PMID- 33052020
OWN - NLM
STAT- PubMed-not-MEDLINE
DCOM- 20201217
LR  - 20201217
IS  - 1861-471X (Electronic)
IS  - 1861-471X (Linking)
VI  - 15
IP  - 24
DP  - 2020 Dec 14
TI  - Photo-induced sp(3) C-H bond arylation, cyanation and nitroalkylation of 
      tetrahydroisoquinolines (THIQs) under visible light irradiation using a 
      combination of NHPI and Rose Bengal.
PG  - 4302-4306
LID - 10.1002/asia.202000999 [doi]
AB  - This work reports a sustainable protocol for alpha-arylation of 
      tetrahydroisoquinolines (THIQs) with aryl diazonium salts using a combination of 
      a cheap and stable oxidant, N-hydroxyphthalimide (NHPI), and an inexpensive dye 
      photosensitizer, Rose Bengal (RB), for the first time. The reaction was performed 
      at ambient temperature using green LED light irradiation under an oxygen 
      atmosphere. The developed alpha-arylation protocol shows a diverse substrate scope 
      for various THIQs and aryl diazonium salts. The work also explores 
      nitroalkylation and cyanation under the developed reaction conditions. A possible 
      SET mechanism is involved which was confirmed by ESI-MS analysis of the reaction 
      mixture.
CI  - (c) 2020 Wiley-VCH GmbH.
FAU - Patil, Mahendra R
AU  - Patil MR
AD  - Department of Chemistry, Institute of Chemical Technology, Nathalal Parekh road, 
      Matunga, Mumbai, 400019, India.
FAU - Shah, Jagrut
AU  - Shah J
AD  - Department of Chemistry, Institute of Chemical Technology, Nathalal Parekh road, 
      Matunga, Mumbai, 400019, India.
FAU - Kumar, A Vijay
AU  - Kumar AV
AD  - Department of Chemistry, Institute of Chemical Technology, Nathalal Parekh road, 
      Matunga, Mumbai, 400019, India.
FAU - Kapdi, Anant R
AU  - Kapdi AR
AD  - Department of Chemistry, Institute of Chemical Technology, Nathalal Parekh road, 
      Matunga, Mumbai, 400019, India.
LA  - eng
PT  - Journal Article
DEP - 20201119
PL  - Germany
TA  - Chem Asian J
JT  - Chemistry, an Asian journal
JID - 101294643
SB  - IM
OTO - NOTNLM
OT  - Cross dehydrogenative coupling
OT  - Green LED
OT  - NHPI
OT  - Photo Redox Catalysis
OT  - Rose Bengal
EDAT- 2020/10/15 06:00
MHDA- 2020/10/15 06:01
CRDT- 2020/10/14 09:20
PHST- 2020/08/22 00:00 [received]
PHST- 2020/10/12 00:00 [revised]
PHST- 2020/10/15 06:00 [pubmed]
PHST- 2020/10/15 06:01 [medline]
PHST- 2020/10/14 09:20 [entrez]
AID - 10.1002/asia.202000999 [doi]
PST - ppublish
SO  - Chem Asian J. 2020 Dec 14;15(24):4302-4306. doi: 10.1002/asia.202000999. Epub 
      2020 Nov 19.