Palladium(0) catalysis in hydrostannation of carbon-carbon triple bonds

Cochran, John C.; Bronk, Brian S.; Terrence, Kathleen M.; Phillips, Harmony K.

doi:10.1016/s0040-4039(00)97130-2

Cited by 58 publications

(26 citation statements)

References 15 publications

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“…82 Alkynyl esters are a generally reliable substrate class with palladium catalysis, providing the (E)-a-stannyl enoate in useful selectivity and yield. 82,116,117 A few representative examples are shown in Table 30.…”

Section: Scheme 47 Isomer Effects On Hydrostannationmentioning

confidence: 99%

Addition of Metalloid Hydrides to Alkynes: Hydrometallation with Boron, Silicon, and Tin

Trost¹,

Ball²

2005

Synthesis

372

218

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Section: Scheme 47 Isomer Effects On Hydrostannationmentioning

confidence: 99%

Addition of Metalloid Hydrides to Alkynes: Hydrometallation with Boron, Silicon, and Tin

Trost¹,

Ball²

2005

Synthesis

372

218

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“…Conjugated alkynones , also exhibit good to excellent regioselectivity for the formation of the α-isomer, but the level of selectivity seems to depend on the nature of the tin hydride employed. The reaction with Bu 3 SnH provided a 82:18 mixture of α- and β-( E )-isomers whereas the use of Me 3 SnH furnishes exclusively the α-isomer (Scheme ). Although the reaction with Me 3 SnD is also regioselective, it is not stereoselective and provides a 1:1 mixture of α-( Z ) and α-( E )-isomers .…”

Section: Scope and Limitationsmentioning

confidence: 99%

Hydrostannation of Alkynes

2019

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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.

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“…Addition of tin hydride can proceed via either a radical or an ionic pathway, depending on the reaction conditions and the substituents adjacent to the π-bond. 8 The ester gives predominantly syn (kinetic) addition, while the ketone gives predominantly anti (thermodynamic) addition. Hydrostannation of terminal alkynes can form three products (eq 1).…”

Section: Hydrostannationmentioning

confidence: 99%