Highly Regiocontrolled and Efficient Synthesis of Vinyl- and Allylstannanes via Lewis Acids and Pd-Catalyzed Hydrostannation of Allenes: Scope and Limitations

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Abstract
The hydrostannation of allenes 1 with tributylstannyl hydride in the presence of B(C6F5)3 catalyst produced vinylstannanes 2 regioselectively, whereas the hydrostannation of 1 with tributylstannyl and triphenylstannyl hydride in the presence of Pd(PPh3)4 catalyst gave allylstannanes 5,6 regio- and stereo (in certain cases)-selectively. The mechanisms for these catalytic reactions were proposed.