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Iridium Catalyst System for Transfer Hydrogenation. Wu Hua 2012-6-9. Iridium Hydride Complex Catalyzed Addition of Nitriles to Carbon-Nitrogen Triple Bonds of Nitriles.

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slide2

Iridium Hydride Complex Catalyzed Addition of Nitriles to Carbon-Nitrogen Triple Bonds of Nitriles

A mixture of nucleophile (1.0 mmol), nitrile (2.0 mmol), and IrH(CO)(PPh3)3 (3 mol %) in dry THF (0.25 mL) was stirred at 120 °C for 12 h under argon.

Mechanism:

Shun-Ichi Murahashi. J. Am. Chem. Soc. 1998, 120, 4244-4245

slide3

A Three-Component Coupling Reaction of Aldehydes, Amines, and Alkynes

Yasutaka Ishii. Angew. Chem. Int. Ed. 2001, 40, 2534-2536

slide4

N-Alkylation of amines with alcohols catalyzed by a Cp*Ir complex

Substrates:

Ken-ichi Fujita, Ryohei Yamaguchi. Tetrahedron Letters. 2003, 44, 2687–2690

slide6

An Efficient Direct r-Alkylation of Ketones with Primary Alcohols Catalyzed by [Ir(cod)Cl]2/PPh3/KOH System without Solvent

Kazuhiko Taguchi, Yasutaka Ishii. J. Am. Chem. Soc. 2004, 126, 72-73

slide8

Mechanism:

Kazuhiko Taguchi, Yasutaka Ishii. J. Am. Chem. Soc. 2004, 126, 72-73

slide9

Catalytic Reductive Alkylation of Secondary Amine with Aldehyde and Silane by an Iridium Compound

Tomoya Mizuta, Satoshi Sakaguchi, and Yasutaka Ishii. J. Org. Chem. 2005, 70, 2195-2199

slide10

Plausible Mechanism:

Tomoya Mizuta, Satoshi Sakaguchi, and Yasutaka Ishii. J. Org. Chem. 2005, 70, 2195-2199

slide11

Guerbet Reaction of Primary Alcohols

Mechanism of Guerbet reaction:

Yasutaka Ishii. J. Org. Chem. 2006, 71, 8306-8308

slide12

New Coupling Reaction of Secondary Amines, Aldehydes, and Alkynes Catalyzed by an

Iridium Complex

Mechanism:

Yasutaka Ishii.Org. Lett. 2006, 8, 2459-2462

slide13

Oxidative dimerization of primary alcohols to esters catalyzed by iridium complexes

Yasutaka Ishii. Tetrahedron Lett. 2006, 47, 9199–9201

slide14

Alkylation of active methylene compounds with alcohols catalyzed by an iridium complex

Mechanism:

Yasutaka Ishii. Chem. Commun. 2007, 2850–2852

slide15

Synthesis of Diketones and ω -Hydroxy Ketones from Methyl Ketones and , α,ω –Diols by an [IrCl(cod)]2/PPh3/KOH System

Yasutaka Ishii. Bull. Chem. Soc. Jpn. 2008, 81, 689–696

Iridium-Catalyzed α-Alkylation of Acetates with Primary Alcohols and Diols

Yasutaka Ishii. J. Am. Chem. Soc. 2010, 132, 2536–2537

slide16

N-Heterocyclization of Naphthylamines with 1,2- and 1,3-Diols Catalyzed by an Iridium Chloride/BINAP System

Yasutaka Ishii. J. Org. Chem. 2009, 74, 628–633

slide18

Iridium-Catalyzed Coupling Reaction of Primary Alcohols with 1-Aryl-1-propynes

Leading to Secondary Homoallylic Alcohols

Yasutaka Ishii. Org. Lett., 2009, 11, 3510-3513

slide19

Iridium-Catalyzed Coupling Reaction of Primary Alcohols with 1-Aryl-1-propynes

Leading to Secondary Homoallylic Alcohols

A Plausible Reaction Mechanism:

Yasutaka Ishii. Org. Lett., 2009, 11, 3510-3513

Yasutaka Ishii. Chem. Eur. J. 2010, 16, 1883 – 1888

slide20

Iridium-Catalyzed Reactions of w-Arylalkanols to α,ω –DiarylalkanesDiarylalkanes

Yasutaka Ishii. Angew. Chem. Int. Ed. 2011, 50, 8618 –8622

slide22

Summary

a. Reaction Temperature

b. Rh, Ru, Ni

c. Development of hydrogen transfer reactions