Fig. 7: Substrate scope and examining the functional group compatibility.

Standard conditions: Alkyne (1.0 equiv., 0.1 mmol), Pd-N4/CN (2 wt%, 10 mg), TEOA (0.5 mL), H2O (2 mL), DCE (2 mL), rt, Ar, 4 h, 420 nm LEDs, isolated yield. The by-products were detected by GC or HPLC and 1H NMR analysis. aThe scale-up reaction: 1 (1.0 equiv., 1 mmol), Pd-N4/CN (2 wt%, 50 mg), TEOA (5 mL), H2O (20 mL), DCE (20 mL), rt, Ar, 12 h, 420 nm LEDs. bYields were determined by GC analysis using biphenyl as the internal standard. n.d. = not detected. Intermolecular reaction screening: 1 (1.0 equiv., 0.1 mmol), additive (1.0 equiv., 0.1 mmol), Pd-N4/CN (2 wt%, 10 mg), TEOA (0.5 mL), H2O (2 mL), DCE (2 mL), rt, Ar, 4 h, 420 nm LEDs. The yields and recoveries were determined by GC analysis using biphenyl as the internal standard. Green ‘√’ ( > 66%), yellow ‘−’ (34-66%), red ‘×’ ( < 34%).