Access to 1,1‐Diborylalkenes and Concomitant Stereoselective Reactivity

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Gem‐diborylalkenes have emerged as efficient reagents for selective cross‐coupling reactions, reduction approaches and Michael additions. The synthesis of 1,1‐diborylalkenes involves condensation of polyborated compounds with aldehydes or ketones followed by B–O elimination, geminal diboration of 1,1‐dihaloalkenes, 1‐haloalkenes or terminal alkynes, dehydrogenative borylation of alkenes, borylation of alkynylboronates and hydroboration of alkynylboronates. These new sets of reactions are general for a wide range of substrates and they can be understood to have complementary mechanisms.