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The decarboxylative C−H/C−O functionalization was accomplished by air‐ and water‐tolerant manganese(I) catalysis. The versatile C−H allylation occurred by facile organometallic C−H metalation on indoles, arenes, amino acids and synthetically meaningful aryl ketimines with ample substrate scope and high levels of chemo‐, site‐ and regio‐selectivity.