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We present a method for the generation of boron-containing unsaturated small moleculesviahexamethylbenzene elimination. 

Herein, we report boron-centered reductive elimination reactions to afford cyclic(alkyl)(amino) carbene (CAAC)-ligated chloroborylene and bromoborylene. 

Diazo compounds and organic azides are widely used as reagents for accessing valuable molecules in multiple areas of fundamental and applied chemistry. Their capacity to undergo versatile chemical transformations arises from the reactive nature of an incipient dinitrogen molecule at the terminal position. In this work, we report the synthesis and characterization of an N-heterocyclic carbene (NHC)–stabilized diazoborane—a boron-centered analog of organic azides and diazoalkanes. The diazoborane displays a strong tendency to release dinitrogen, thus serving as a borylene source, in analogy to organic azides and diazoalkanes serving as nitrene and carbene sources, respectively. Also reminiscent of diazoalkane and organic azide reactivity, the diazoborane serves as a 1,3-dipole that undergoes uncatalyzed [3+2] cycloaddition with an unactivated terminal alkyne, affording a five-membered heterocycle after a two-step rearrangement.