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Peer-reviewedCC BY 4.0Chemistry (Weinheim an Der Bergstrasse, Germany)

Infrared Irradiation‐Assisted Pd‐Catalyzed C(sp3)─H Arylation and Tandem Cyclization of Ortho‐Tolualdehydes

  • Matteo Renato Martina1
  • Ambra Maria Fiore1
  • Angela Punzi1
  • Gianluigi Albano1,2
  • Roberta Ragni1
  • Pietro Cotugno1
  • Gianluca Maria Farinola1
  1. 1Dipartimento Di Chimica Università Degli Studi di Bari Aldo Moro Bari Italy
  2. 2Dipartimento Di Scienze Chimiche, Della Vita e della Sostenibilità Ambientale Università Di Parma Parma Italy
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Abstract

Herein, we describe the use of IR irradiation to promote Pd‐catalyzed C(sp3)─H arylation and tandem C(sp3)─H arylation/electrophilic aromatic cyclization of ortho‐tolualdehydes with aryl iodides via a transient directing group (TDG) strategy. The optimized conditions employ Pd(OAc)2 (10 mol%) as the catalyst, glycine (40 mol%) as the TDG, and AgTFA (1.5 equiv.) as the additive in an AcOH/H2O (9:1, v/v) solvent mixture under irradiation with a 250 W IR lamp. The reaction time (30 min) is considerably shorter than previously reported reaction times for similar reactions performed under thermal heating (12–48 h, 90°C–130°C). The reaction outcome under infrared (IR) irradiation strongly depends on the electronic nature of the substituents on the aryl iodides: electron‐withdrawing groups at any position and electron‐donating groups at the ortho and/or para positions favor the Pd‐catalyzed C(sp3)─H arylation, leading to 2‐benzylbenzaldehydes, whereas, in the presence of electron‐donating groups at the meta‐position, a tandem C(sp3)─H arylation/electrophilic aromatic cyclization occurs, producing substituted anthracenes.

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Cite

BibTeXRIS
BibTeX
@article{martina2026infrared,
  title = {{Infrared Irradiation‐Assisted Pd‐Catalyzed C(sp3)─H Arylation and Tandem Cyclization of Ortho‐Tolualdehydes}},
  author = {Matteo Renato Martina and Ambra Maria Fiore and Angela Punzi and Gianluigi Albano and Roberta Ragni and Pietro Cotugno and Gianluca Maria Farinola},
  journal = {Chemistry (Weinheim an Der Bergstrasse, Germany)},
  year = {2026},
  month = aug,
  doi = {10.1002/chem.71564},
  url = {https://doi.org/10.1002/chem.71564},
  note = {CC BY 4.0},
}
RIS
TY  - JOUR
TI  - Infrared Irradiation‐Assisted Pd‐Catalyzed C(sp3)─H Arylation and Tandem Cyclization of Ortho‐Tolualdehydes
AU  - Matteo Renato Martina
AU  - Ambra Maria Fiore
AU  - Angela Punzi
AU  - Gianluigi Albano
AU  - Roberta Ragni
AU  - Pietro Cotugno
AU  - Gianluca Maria Farinola
PY  - 2026
DA  - 2026/08/12
JO  - Chemistry (Weinheim an Der Bergstrasse, Germany)
DO  - 10.1002/chem.71564
UR  - https://doi.org/10.1002/chem.71564
AB  - Herein, we describe the use of IR irradiation to promote Pd‐catalyzed C(sp3)─H arylation and tandem C(sp3)─H arylation/electrophilic aromatic cyclization of ortho‐tolualdehydes with aryl iodides via a transient directing group (TDG) strategy. The optimized conditions employ Pd(OAc)2 (10 mol%) as the catalyst, glycine (40 mol%) as the TDG, and AgTFA (1.5 equiv.) as the additive in an AcOH/H2O (9:1, v/v) solvent mixture under irradiation with a 250 W IR lamp. The reaction time (30 min) is considerably shorter than previously reported reaction times for similar reactions performed under thermal heating (12–48 h, 90°C–130°C). The reaction outcome under infrared (IR) irradiation strongly depends on the electronic nature of the substituents on the aryl iodides: electron‐withdrawing groups at any position and electron‐donating groups at the ortho and/or para positions favor the Pd‐catalyzed C(sp3)─H arylation, leading to 2‐benzylbenzaldehydes, whereas, in the presence of electron‐donating groups at the meta‐position, a tandem C(sp3)─H arylation/electrophilic aromatic cyclization occurs, producing substituted anthracenes.
SN  - 0947-6539
SN  - 1521-3765
ER  -