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Formation of C–C Bonds via Iridium-Catalyzed Hydrogenation and Transfer Hydrogenation

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Iridium Catalysis

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 34))

Abstract

The formation of C–C bonds via catalytic hydrogenation and transfer hydrogenation enables carbonyl and imine addition in the absence of stoichiometric organometallic reagents. In this review, iridium-catalyzed C–C bond-forming hydrogenations and transfer hydrogenations are surveyed. These processes encompass selective, atom-economic methods for the vinylation and allylation of carbonyl compounds and imines. Notably, under transfer hydrogenation conditions, alcohol dehydrogenation drives reductive generation of organoiridium nucleophiles, enabling carbonyl addition from the aldehyde or alcohol oxidation level. In the latter case, hydrogen exchange between alcohols and π-unsaturated reactants generates electrophile–nucleophile pairs en route to products of hydro-hydroxyalkylation, representing a direct method for the functionalization of carbinol C–H bonds.

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Notes

  1. 1.

    The catalytic hydrogenation of atmospheric nitrogen, accounts for the annual production of over 100,000,000 metric tons of ammonia, which is the limiting nutrient in terrestrial plant growth. The Haber–Bosch process is estimated to sustain one-third of the Earth’s population. Approximately half the nitrogen in our bodies is nitrogen fixed through the Haber–Bosch reaction.

  2. 2.

    The prototypical C–C bond forming hydrogenation, hydroformylation combines basic feedstocks (α-olefins, carbon monoxide, and hydrogen) with perfect atom economy and accounts for the production of over 10 million metric tons of aldehyde annually, making it the largest volume application of homogeneous metal catalysis.

  3. 3.

    The asymmetric hydrogenation of C=X π-bonds (X = O, NR) is estimated to account for over half the chiral drugs manufactured industrially, withstanding physical and enzymatic resolution.

  4. 4.

    For selected reviews on C–C bond forming hydrogenation and transfer hydrogenation, see [11–17].

  5. 5.

    Prior to our systematic studies, two isolated reports of hydrogen mediated C–C coupling were reported, see [18, 19].

  6. 6.

    Side products of reductive C–C bond formation have been observed in catalytic hydrogenation on rare occasions, see [20, 21].

  7. 7.

    The alcohol-unsaturate couplings developed in our laboratory provide products of carbonyl addition. In contrast, related hydrogen auto-transfer processes provide products of alcohol substitution via pathways involving oxidation–condensation–reduction and the use of preactivated nucleophiles. For recent reviews, see [22–25].

  8. 8.

    Processes that enable direct catalytic C–C functionalization of carbinol C–H bonds are highly uncommon. Rh-catalyzed alcohol-vinylarene C–C coupling has been described. The requirement of BF3 and trends in substrate scope suggest these processes involve alcohol dehydrogenation-reductive Prins addition: [26–29].

  9. 9.

    For radical mediated C–C functionalization of carbinol C–H bonds, see [30, 31].

  10. 10.

    For reviews encompassing the synthesis of allylic alcohols, see [32, 33].

  11. 11.

    For reviews encompassing the synthesis of allylic amines, see [34–36].

  12. 12.

    For enantioselective catalytic addition of vinylzinc reagents to aldehydes, see [52–70].

  13. 13.

    For reviews encompassing catalytic enantioselective aldehyde vinylation using organozinc reagents, see [71, 72].

  14. 14.

    For enantioselective copper catalyzed addition of organozinc reagents to imines, see [97–116].

  15. 15.

    Enantioselective Ni-catalyzed alkyne, imine, triethylborane 3-component coupling has been reported, but modest selectivities (51–89% ee) are observed. For this method, vinylation is accompanied by ethyl transfer: [149]

  16. 16.

    For selected reviews encompassing intra- and intermolecular direct reductive coupling of alkynes to carbonyl partners, see [151–158]

  17. 17.

    Alkyne complexation by iridium(I) results in substantial deviation from linearity, as revealed by single crystal X-ray diffraction analysis: [190–194].

  18. 18.

    The bidentate κ2-mode of binding has been observed by single crystal X-ray diffraction analysis for a related palladium N-arylsulfonamidate complex.

  19. 19.

    For selected examples of chirally modified allyl metal reagents, see [207–220].

  20. 20.

    For selected examples of catalytic asymmetric carbonyl allylation employing allylmetal reagents, see [221–224].

  21. 21.

    For selected examples of carbonyl allylations employing nucleophilic π-allyls derived from allylic acetates and carboxylates, see: Palladium [225–233], Rhodium [234, 235], Ruthenium [236–238], Iridium [239–241].

  22. 22.

    For selected reviews on carbonyl allylation via umpolung of π-allyls, see [242–247].

  23. 23.

    For catalytic enantioselective carbonyl allylation and crotylation via Nozaki-Hiyama coupling, see [248–257].

  24. 24.

    For recent reviews of catalytic Nozaki-Hiyama coupling, see [258–261].

  25. 25.

    For reviews on carbonyl-ene reactions, see [262–265].

  26. 26.

    For Nickel catalyzed carbonyl-ene reactions, see [266–268].

  27. 27.

    Under the conditions of ruthenium catalysis, alcohols and allylic acetates couple to form enones, see [284].

  28. 28.

    For (hydroxymethyl)allylation via palladium catalyzed reductive coupling of allylic carboxylates, see [302–304].

  29. 29.

    For (hydroxymethyl)allylation via palladium catalyzed reductive coupling of vinyl epoxides, see [305, 306].

  30. 30.

    For catalytic enantioselective (hydroxymethyl)allylation, see [307, 308].

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Acknowledgments

Acknowledgment is made to the Robert A. Welch Foundation (F-0038), NIH-NIGMS (RO1-GM69445), and the ACS-GCI Pharmaceutical Roundtable for partial support of the research described in this account. Dr Oliver Briel of Umicore is thanked for the generous donation of iridium salts. Dr Wataru Kuriyama and Dr Yasunori Ino of Takasago are thanked for the generous donation of (R)- and (S)-SEGPHOS.

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Authors and Affiliations

  1. Department of Chemistry and Biochemistry, University of Texas at Austin, 1 University Station – A5300, Austin, TX, 78712-0165, USA

    John F. Bower & Michael J. Krische

  2. Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford, 1 3TA, UK

    John F. Bower

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  1. John F. Bower
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Correspondence to Michael J. Krische .

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  1. Dept. Biochemistry & Organic Chemistry, Uppsala University, Uppsala, Sweden

    Pher G. Andersson

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Bower, J.F., Krische, M.J. (2011). Formation of C–C Bonds via Iridium-Catalyzed Hydrogenation and Transfer Hydrogenation. In: Andersson, P. (eds) Iridium Catalysis. Topics in Organometallic Chemistry, vol 34. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-15334-1_5

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