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Using alkynyl hypervalent iodine reagents as carbene precursors and amine\u2013borane adducts as boron sources, this method delivers a broad range of\n                    <jats:italic>E<\/jats:italic>\n                    \u2011configured alkenyl monoborinates in good\u2010to\u2010high yields with exceptional stereoselectivity (&gt;20:1\n                    <jats:italic>E\/Z<\/jats:italic>\n                    ). The reaction proceeds under mild conditions, tolerates diverse aromatic, heteroaromatic, and aliphatic substituents, and is readily scalable to gram quantities. The resulting monoboronate products participate efficiently in a variety of C\u2500X bond\u2011forming transformations, underscoring their synthetic versatility. Initial mechanistic investigations and DFT calculation support the formation of an unsaturated Pd\u2013vinylidene intermediate, with stereocontrol influenced by ligand coordination at the palladium center. 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