Catalytic Reactions by Heterobimetallic Carbonyl Complexes with Polar Metal–Metal Interactions

Abstract

Heterobinuclear catalysts capable of bimetallic cooperative bond activation provide an alternative pathway to approach the discovery of novel and unique reactivity and selectivity in catalytic transformations, complementing more traditional mononuclear precious metal catalysts. This review summarizes recent advances in homogenous catalysis using heterobimetallic carbonyl catalysts with polar metal–metal interactions.

1 Introduction

2 Hydrogenation and Hydrofunctionalization

3 Carbonylation and Carboxylation

4 Oxidative Transformations

5 Conclusion and Outlook

Key words

heterobinuclear catalysts - metal carbonyl anions - metal–metal interactions - cooperative bond activation

Publication History

Received: 08 December 2020

Accepted after revision: 17 December 2020

Accepted Manuscript online:
17 December 2020

Article published online:
25 January 2021

• References

• 1a Allen AE, MacMillan DW. C. Chem. Sci. 2012; 3: 633
• 1b Lee JM, Na Y, Han H, Chang S. Chem. Soc. Rev. 2004; 33: 302
• 1c Karunananda MK, Mankad NP. ACS Catal. 2017; 7: 6110
• 1d van der Vlugt JI. Eur. J. Inorg. Chem. 2011; 363
• 1e Park J, Hong S. Chem. Soc. Rev. 2012; 41: 6913
• 1f Xiong N, Zhang G, Sun X, Zeng R. Chin. J. Chem. 2020; 38: 185
• 1g Fontaine FG, Stephan DW. Philos. Trans. R. Soc. London, Ser. A 2017; 375: 20170004
• 1h Gunanathan C, Milstein D. Acc. Chem. Res. 2011; 44: 588
• 1i Powers IG, Uyeda C. ACS Catal. 2017; 7: 936
• 1j Buchwalter P, Rosé J, Braunstein P. Chem. Rev. 2015; 115: 28
• 2a Chatterjee B, Chang W.-C, Jena S, Werlé C. ACS Catal. 2020; 10: 14024
• 2b Campos J. Nat. Rev. Chem. 2020; 4: 696
• 2c Pye DR, Mankad NP. Chem. Sci. 2017; 8: 1705
• 2d Kim UB, Jung DJ, Jeon HJ, Rathwell K, Lee S.-g. Chem. Rev. 2020; 120: 13382
• 3a Ogo S, Ichikawa K, Kishima T, Matsumoto T, Nakai H, Kusaka K, Ohhara T. Science 2013; 339: 682
• 3b Simmons TR, Berggren G, Bacchi M, Fontecave M, Artero V. Coord. Chem. Rev. 2014; 270–271: 127
• 4 Jeoung JH, Dobbek H. Science 2007; 318: 1461
• 5 Collman JP, Devaraj NK, Decréau RA, Yang Y, Yan Y.-L, Ebina W, Eberspacher TA, Chidsey CE. D. Science 2007; 315: 1565
• 6 King RB. J. Organomet. Chem. 1975; 100: 111
• 7 Gade LH. Angew. Chem. Int. Ed. 2000; 39: 2658
• 8 Mankad NP. Chem. Commun. 2018; 54: 1291
• 9 Parmelee SR, Mankad NP. Dalton Trans. 2015; 44: 17007
• 10 Karunananda MK, Parmelee SR, Waldhart GW, Mankad NP. Organometallics 2015; 34: 3857
• 11a Mazzacano TJ, Leon NJ, Waldhart GW, Mankad NP. Dalton Trans. 2017; 46: 5518
• 11b Levina VA, Rossin A, Belkova NV, Chierotti MR, Epstein LM, Filippov OA, Gobetto R, Gonsalvi L, Lledós A, Shubina ES, Zanobini F, Peruzzini M. Angew. Chem. Int. Ed. 2010; 50: 1367
• 12 Schmidt JA. R, Lobkovsky EB, Coates GW. J. Am. Chem. Soc. 2005; 127: 11426
• 13 Banerjee S, Karunananda MK, Bagherzadeh S, Jayarathne U, Parmelee SR, Waldhart GW, Mankad NP. Inorg. Chem. 2014; 53: 11307
• 14 Karunananda MK, Vázquez FX, Alp EE, Bi W, Chattopadhyay S, Shibata T, Mankad NP. Dalton Trans. 2014; 43: 13661
• 15 Pinkes JR, Steffey BD, Vites JC, Cutler AR. Organometallics 1994; 13: 21
• 16 Karunananda MK, Mankad NP. Organometallics 2017; 36: 220
• 17 Beers OC. P, Bouman MM, Komen AE, Vrieze K, Elsevier CJ, Horn E, Spek AL. Organometallics 1993; 12: 315
• 18 Man ML, Zhou Z, Ng SM, Lau CP. Dalton Trans. 2003; 3: 3727
• 19a Cheng T.-Y, Bullock RM. Organometallics 2002; 21: 2325
• 19b Cheng T.-Y, Brunchwig BS, Bullock RM. J. Am. Chem. Soc. 1998; 120: 13121
• 19c Moore EJ, Sullivan JM, Norton JR. J. Am. Chem. Soc. 1986; 108: 2257
• 19d Kristjánsdóttir SS, Norton JR. In Transition Metal Hydrides, , Dedieu A, Chap. 9. Wiley-VCH; New York: 1992
• 20 Karunananda MK, Mankad NP. J. Am. Chem. Soc. 2015; 137: 14598
• 21 Abraham J, Jordan AJ, Lalic G, Sadighi JP. Chem. Rev. 2016; 116: 8318
• 22 Zhang Y, Karunananda MK, Yu H.-C, Clark KJ, Williams W, Mankad NP, Ess DH. ACS Catal. 2019; 9: 2657
• 23 Yao C, Dahmen T, Gansäuer A, Norton J. Science 2019; 364: 764
• 24 Ye S, Leong WK. J. Organomet. Chem. 2006; 691: 1216
• 25 Cheng LJ, Mankad NP. J. Am. Chem. Soc. 2019; 141: 3710
• 26 Yu H.-C, Islam SM, Mankad NP. ACS Catal. 2020; 10: 3670
• 27a Zhang Z.-Z, Xi H.-P, Zhao W.-J, Jiang K.-Y, Wang H.-G, Wang R.-J, Wu Y. J. Organomet. Chem. 1993; 454: 221
• 27b Fujuoka A, Ichikawa M, Hriljac JA, Shriver DF. Inorg. Chem. 1987; 26: 3645
• 28 Drent E, Kragtwijk E. (Shell Internationale Research Maatschappij B.V.). Eur. Pat. Appl. EP 0577206B1, 1998 , Chem. Abstr. 1994, 120, 191517c.
• 29 Getzler YD. Y. L, Mahadevan V, Lobkovsky EB, Coates GW. J. Am. Chem. Soc. 2002; 124: 1174
• 30 Church TL, Getzler YD. Y. L, Coates GW. J. Am. Chem. Soc. 2006; 128: 10125
• 31 King RB. Acc. Chem. Res. 1970; 3: 417
• 32 Mulzer M, Whiting BT, Coates GW. J. Am. Chem. Soc. 2013; 135: 10930
• 33 Mulzer M, Ellis WC, Lobkovsky EB, Coates GW. Chem. Sci. 2014; 5: 1928
• 34 Hubbell AK, LaPointe AM, Lamb JR, Coates GW. J. Am. Chem. Soc. 2019; 141: 2474
• 35 Lamb JR, Hubbell AK, MacMillan SN, Coates GW. J. Am. Chem. Soc. 2020; 142: 8029
• 36a Heck RF, Breslow DS. J. Am. Chem. Soc. 1963; 85: 2779
• 36b Pye DR, Cheng L.-J, Mankad NP. Chem. Sci. 2017; 8: 4750
• 37 Man ML, Lam KC, Sit WN, Ng SM, Zhou Z, Lin Z, Lau CP. Chem. Eur. J. 2006; 12: 1004
• 38 Bagherzadeh S, Mankad NP. J. Am. Chem. Soc. 2015; 137: 10898
• 39 Shintani R, Nozaki K. Organometallics 2013; 32: 2459
• 40a Braunstein P, Morise X. Organometallics 1998; 17: 540
• 40b Braunstein P, Knorr M, Piana H, Schubert U. Organo­metallics 1991; 10: 828
• 41 Mazzacano TJ, Mankad NP. J. Am. Chem. Soc. 2013; 135: 17258
• 42a Waltz KM, He W, Muhoro C, Hartwig JF. J. Am. Chem. Soc. 1995; 117: 11357
• 42b Waltz KM, Muhoro CN, Hartwig JF. Organometallics 1999; 18: 3383
• 43 Parmelee SR, Mazzacano TJ, Mankad NP, Keith JA. ACS Catal. 2015; 5: 3689
• 44 Straub T, Koskinen AM. P. Inorg. Chem. Commun. 2002; 5: 1052
• 45 Braunstein P, Clerc G, Morise X. New J. Chem. 2003; 27: 68