ABSTRACT Herein, we describe the use of IR irradiation to promote Pd‐catalyzed C(sp 3 )─H arylation and tandem C(sp 3 )─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/H 2 O (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(sp 3 )─H arylation, leading to 2‐benzylbenzaldehydes, whereas, in the presence of electron‐donating groups at the meta ‐position, a tandem C(sp 3 )─H arylation/electrophilic aromatic cyclization occurs, producing substituted anthracenes.