In this paper, we report a synthetic protocol for the construction of biaryl motif-based or π-extended azobenzene and alkylated azobenzene derivatives via the Pd(II)-catalyzed bidentate directing group (DG)-aided C-H activation and functionalization strategy. In the past, the synthesis of biaryl motif-based azobenzenes was accomplished through the traditional cross-coupling reaction involving organometallic reagents and aryl halides or equivalent coupling partners. We have shown the direct coupling of C-H bonds of aromatic/aliphatic carboxamides (possessing DG) with iodoazobenzenes as the coupling partners through the Pd(II)-catalyzed bidentate DG-aided, site-selective C-H functionalization method. Azobenzene-containing compounds are a versatile class of photo-responsive molecules that have found applications across branches of chemical-, biological and material sciences and are prevalent in medicinally relevant molecules. Accordingly, the synthesis of new and functionalized azobenzene-based scaffolds has been an attractive topic of research. While the classical methods are efficiently used but classical methods need pre-functionalized starting materials. This protocol involving the Pd(II)-catalyzed, directing group-aided site-selective C-H arylation of aromatic and aliphatic carboxamides using iodoazobenzene as the coupling partners affording azobenzene-based carboxamides is an additional route and also contribution towards enriching the library of modified azobenzenes. We have also shown the photoswitching properties of representative compounds synthesized via the Pd(II)-catalyzed directing group-aided site-selective C-H functionalization method.

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