Hydrostannation of Alkynes

Mouad Alami (1) , Abdallah Hamze (1) , Olivier Provot (1)

1 BioCIS - Biomolécules : Conception, Isolement, Synthèse

In this review, we present an overview of hydrostannation of alkynes until the end of 2018. Mechanism of the tin hydride addition on a triple bond is discussed at the beginning of this review in the presence of metal catalysts as Pd, Ru-based complexes, Lewis acids and under radical conditions. Then, stereoselectivity as well as regioselectivity aspects of tin hydride addition on the carbon triple bond is discussed using metal-catalysis, radical conditions or Lewis acids. In each of these items, the reactions will be studied for terminal alkynes and then, for internal alkynes. Applications of hydrostannation of alkynes using metal-catalysis is presented in a variety of total syntheses with Pd, Mo, Rh and Ru-complexes to provide highly functionalized vinyl stannanes derivatives as key-intermediates. Comparison with other methods providing vinyl stannanes using metallostannation followed by protonation is presented before the last section dealing with a summary of classical experimental conditions used to achieve the hydrostannation of alkynes.

Keywords: hydrostannation; alkyne; catalysis; stereoselectivity; regioselectivity; tin

Domains: Organic chemistry; Catalysis

Mouad Alami, Abdallah Hamze, Olivier Provot. Hydrostannation of Alkynes. ACS Catalysis, 2019, 9 (4), pp.3437-3466. ⟨10.1021/acscatal.9b00482⟩. ⟨hal-02394188⟩