Oxidative Addition, Reductive Elimination

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Presentation transcript:

Oxidative Addition, Reductive Elimination Oxidative addition, reductive elimination Heck reaction, Suzuki coupling Concerted addition Often with H2, alkanes, R3SiH, O2 Stepwise Often with HX, R3SnX, alkyl acyl and allyl halides and an electron-rich metal (IrI, RhI, Pd(0)) 8/13/2019 Oxidative Addition, Reductive Elimination

Oxidative addition, reductive elimination Sometimes radical mechanism: Test: Formation R-R CIDNP 8/13/2019 Oxidative Addition, Reductive Elimination

Oxidative addition, reductive elimination Promote oxidative addition: Strongly basic metal fragment Concerted: weak, apolar s bond Stepwise: polar bond, good leaving group C-H: arene > alkane 8/13/2019 Oxidative Addition, Reductive Elimination

Oxidative Addition, Reductive Elimination The Heck reaction 8/13/2019 Oxidative Addition, Reductive Elimination

Oxidative Addition, Reductive Elimination The Heck reaction 8/13/2019 Oxidative Addition, Reductive Elimination

Suzuki and Stille coupling 8/13/2019 Oxidative Addition, Reductive Elimination

Suzuki and Stille coupling 8/13/2019 Oxidative Addition, Reductive Elimination

Reductive elimination Usually easy for: H + alkyl / aryl / acyl alkyl + acyl SiR3 + alkyl etc Often slow for: alkoxide + alkyl halide + alkyl 8/13/2019 Oxidative Addition, Reductive Elimination

Oxidative Addition, Reductive Elimination Hydrogenation (1) Variation: direct s-bond metathesis of M-R with H2 8/13/2019 Oxidative Addition, Reductive Elimination

Oxidative Addition, Reductive Elimination Hydrogenation (2) (what is wrong with this cycle?) 8/13/2019 Oxidative Addition, Reductive Elimination

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