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Aluminum‐Catalyzed Selective Reduction of Heteroallenes Through Hydroboration: Amide/Thioamide/Selenoamide Bond Construction and C=X (X= O, S, Se) Bond Activation

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An unprecedented conjugated bis-guanidinate (CBG) stabilized aluminum dihydride, [LAlH 2 ; (L = {(ArNH)(ArN)– C=N–C=(NAr)(NHAr)}; Ar = 2,6- Et 2 -C 6 H 3 )] ( I ) catalyzed chemoselective hydroboration of heteroallenes such as carbodiimide (CDI)s, isocyanates, isothiocyanates, and isoselenocyanates is reported. A wide range of heteroallenes, including electron-donating and withdrawing groups, experience hydroboration to obtain selectively N-boryl amide, N-borylaminal, and N-boryl methyl amine products. More importantly, a single sustainable molecular aluminum-based catalyst effectively catalyzes CDIs, isocyanates, isothiocyanates, and isoselenocyanates into formamidines, formamides, thioformamides, and selenoformamides, respectively. Further, heteroallene substrates undergo hydrodeoxygenation (HDO), hydrodesulfurization (HDS), and hydrodeselenization (HDSe) reactions leading to N-boryl methyl amines. In addition, a series of control and kinetic experiments indicate that the aluminum hydride species are essential for all partial and complete reduction steps and breaking the C=X (X = O, S, and Se) bonds in heteroallenes.

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