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Although extensive studies with mostly transition metal\u2010based catalysts have enabled it to produce a broad scope\u00a0of alkenes, a SciFinder\n                    <jats:sup>TM<\/jats:sup>\n                    search and a robustness screen of Lindlar's catalyst indicate that highly Lewis\u2010basic nitrogen\u2010 and sulfur\u2010containing motifs, which are prevalent in drugs, remain problematic. Herein, we report an alkyne semi\u2010reduction using an organic photoreductant that tolerates all 10 of the most common Lewis\u2010basic motifs in drugs. The reaction reduces terminal alkyl and aryl, dialkyl, alkyl aryl, and diaryl alkynes in high yields and\n                    <jats:italic>Z\u2010<\/jats:italic>\n                    selectivities, while tolerating other reducible motifs like sulfones, nitriles, ketones, and electron\u2010poor arenes. 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