Cooperative Hydrogen Atom Transfer: From Theory to Applications

Padmanabha V. Kattamuri; Julian G. West

doi:10.1055/a-1463-9527

Synlett, Inhaltsverzeichnis

Synlett 2021; 32(12): 1179-1186
DOI: 10.1055/a-1463-9527

synpacts

Cooperative Hydrogen Atom Transfer: From Theory to Applications

Padmanabha V. Kattamuri

,

Julian G. West ∗

Abstract

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Dedicated with respect and admiration to Prof. Harry B. Gray on the occasion of his 85^th birthday

Abstract

Hydrogen atom transfer (HAT) is one of the fundamental transformations of organic chemistry, allowing the interconversion of open- and closed-shell species through the concerted movement of a proton and an electron. Although the value of this transformation is well appreciated in isolation, with it being used for homolytic C–H activation via abstractive HAT and radical reduction via donative HAT, cooperative HAT (cHAT) reactions, in which two hydrogen atoms are removed or donated to vicinal reaction centers in succession through radical intermediates, are comparatively unknown outside of the mechanism of desaturase enzymes. This tandem reaction scheme has important ramifications in the thermochemistry of each HAT, with the bond dissociation energy (BDE) of the C–H bond adjacent to the radical center being significantly lowered relative to that of the parent alkane, allowing each HAT to be performed by different species. Herein, we discuss the thermodynamic basis of this bond strength differential in cHAT and demonstrate its use as a design principle in organic chemistry for both dehydrogenative (application 1) and hydrogenative (application 2) reactions. We hope that this overview will highlight the exciting reactivity that is possible with cHAT and inspire further developments with this mechanistic approach.

1 Introduction and Theory

2 Application: Dehydrogenative Transformations

3 Application: Alkene Hydrogenation

4 Future Applications of cHAT

Key words

hydrogen atom transfer - cooperative hydrogen atom transfer - cooperative catalysis - radicals - bond strengths - dehydrogenation - hydrogenation

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References
1 Green SA, Crossley SW. M, Matos JL. M, Vásquez-Céspedes S, Shevick SL, Shenvi RA. Acc. Chem. Res. 2018; 51: 2628
2 Banerjee R, Truhlar DG, Dybala-Defratyka A, Paneth P. Hydrogen Atom Transfers in B12 Enzymes . In Hydrogen-Transfer Reactions . Hynes JT, Klinman JP, Limbach H.-H, Schowen RL. Wiley-VCH; Weinheim: 2006: 1473-1495
3 Capaldo L, Quadri LL, Ravelli D. Green Chem. 2020; 22: 3376
4 Mayer JM, Larsen AS, Bryant JR, Wang K, Lockwood M, Rice G, Won T. Non-Organometallic Mechanisms for C–H Bond Oxidation: Hydrogen Atom versus Electron versus Hydride Transfer. In Activation and Functionalization of C–H Bonds. Goldberg KI, Goldman AS. ACS Symposium Series 885; American Chemical Society; Washington DC: 2004: 356-369
5 Nakano Y, Biegasiewicz KF, Hyster TK. Curr. Opin. Chem. Biol. 2019; 49: 16
6 Sarkar S, Cheung KP. S, Gevorgyan V. Chem. Sci. 2020; 11: 12974
7 Stateman LM, Nakafuku KM, Nagib DA. Synthesis 2018; 50: 1569
8 Crossley SW. M, Obradors C, Martinez RM, Shenvi RA. Chem. Rev. 2016; 116: 8912
9 Newcomb M, Toy PH. Acc. Chem. Res. 2000; 33: 449
10 Roth JP, Yoder JC, Won T, Mayer JM. Science 2001; 294: 2524
11 Mayer JM. Acc. Chem. Res. 2011; 44: 36
12 Parada GA, Goldsmith ZK, Kolmar S, Rimgard BP, Mercado BQ, Hammarström L, Hammes-Schiffer S, Mayer JM. Science 2019; 364: 471
13 Bryant JR, Mayer JM. J. Am. Chem. Soc. 2003; 125: 10351
14 Blanksby SJ, Ellison GB. Acc. Chem. Res. 2003; 36: 255
15 West JG, Sorensen EJ. Isr. J. Chem. 2017; 57: 259
16 Roberts BP. Chem. Soc. Rev. 1999; 28: 25
17 Salamone M, Dilabio GA, Bietti M. J. Org. Chem. 2012; 77: 10479
18 Salamone M, Bietti M. Acc. Chem. Res. 2015; 48: 2895
19 Luo YR. Comprehensive Handbook of Chemical Bond Energies 2007
20 West JG, Huang D, Sorensen EJ. Nat. Commun. 2015; 6: 10093
21 Abrams DJ, West JG, Sorensen EJ. Chem. Sci. 2017; 8: 1954
22 Kattamuri PV, West JG. J. Am. Chem. Soc. 2020; 142: 19316
23 Behrouzian B, Buist PH. Prostaglandins Leukotrienes Essent. Fatty Acids 2003; 68: 107
24 Buist PH. Nat. Prod. Rep. 2004; 21: 249
25 Behrouzian B, Fauconnot L, Daligault F, Nugier-Chauvin C, Patin H, Buist PH. Eur. J. Biochem. 2001; 268: 3545
26 Breslow R, Baldwin S, Flechtner T, Kalicky P, Liu S, Washburn W. J. Am. Chem. Soc. 1973; 95: 3251
27 Breslow R, Scholl P. J. Am. Chem. Soc. 1971; 93: 2331
28 Breslow R. Acc. Chem. Res. 1995; 28: 146
29 Bigi MA, Reed SA, White MC. Nat. Chem. 2011; 3: 216
30 Gunanathan C, Milstein D. Science 2013; 341: 1229712
31 Chowdhury AD, Weding N, Julis J, Franke R, Jackstell R, Beller M. Angew. Chem. Int. Ed. 2014; 53: 6477
32 Xu W, Rosini GP, Krogh-Jespersen K, Goldman AS, Gupta M, Jensen CM, Kaska WC. Chem. Commun. 1997; 2273
33 Krogh-Jespersen K, Czerw M, Summa N, Renkema KB, Achord PD, Goldman AS. J. Am. Chem. Soc. 2002; 124: 11404
34 Burk MJ, Crabtree RH, McGrath DV. J. Chem. Soc., Chem. Commun. 1985; 1829
35 Baudry D, Ephritikhine M, Felkin H, Holmes-Smith R. J. Chem. Soc., Chem. Commun. 1983; 788
36 Capaldo L, Ravelli D. Eur. J. Org. Chem. 2017; 2056
37 Ravelli D, Fagnoni M, Fukuyama T, Nishikawa T, Ryu I. ACS Catal. 2018; 8: 701
38 Tzirakis MD, Lykakis IN, Orfanopoulos M. Chem. Soc. Rev. 2009; 38: 2609
39 Hill J. J. Photochem. 1986; 33: 267
40 Halperin SD, Fan H, Chang S, Martin RE, Britton RA. Angew. Chem. Int. Ed. 2014; 53: 4690
41 Ryu I, Tani A, Fukuyama T, Ravelli D, Montanaro S, Fagnoni M. Org. Lett. 2013; 15: 2554
42 Perry IB, Brewer TF, Sarver PJ, Schultz DM, DiRocco DA, MacMillan DW. C. Nature 2018; 560: 70
43 Sarver PJ, Bacauanu V, Schultz DM, DiRocco DA, Lam Y, Sherer EC, MacMillan DW. C. Nat. Chem. 2020; 12: 459
44 Gridnev AA, Ittel SD. Chem. Rev. 2001; 101: 3611
45 Eisenberg DC, Norton JR. Isr. J. Chem. 1991; 31: 55
46 Li G, Kuo JL, Han A, Abuyuan JM, Young LC, Norton JR, Palmer JH. J. Am. Chem. Soc. 2016; 138: 7698
47 Li G, Han A, Pulling ME, Estes DP, Norton JR. J. Am. Chem. Soc. 2012; 134: 14662
48 Schrauzer GN. Acc. Chem. Res. 1968; 1: 97
49 Dempsey JL, Brunschwig BS, Winkler JR, Gray HB. Acc. Chem. Res. 2009; 42: 1995
50 Connolly P, Espenson JH. Inorg. Chem. 1986; 25: 2684
51 Chao T.-H, Espenson JH. J. Am. Chem. Soc. 1978; 100: 129
52 Hu X, Cossairt BM, Brunschwig BS, Lewis NS, Peters JC. Chem. Commun. 2005; 4723
53 Estes DP, Grills DC, Norton JR. J. Am. Chem. Soc. 2014; 136: 17362
54 Cao H, Kuang Y, Shi X, Wong KL, Tan BB, Kwan JM. C, Liu X, Wu J. Nat. Commun. 2020; 11: 1956
55 Iwasaki K, Wan KK, Oppedisano A, Crossley SW. M, Shenvi RA. J. Am. Chem. Soc. 2014; 136: 1300
56 Obradors C, Martinez RM, Shenvi RA. J. Am. Chem. Soc. 2016; 138: 4962
57 King SM, Ma X, Herzon SB. J. Am. Chem. Soc. 2014; 136: 6884
58 Ma X, Herzon SB. Chem. Sci. 2015; 6: 6250
59 Ma X, Herzon SB. Beilstein J. Org. Chem. 2018; 14: 2259
60 Farney EP, Feng SS, Schäfers F, Reisman SE. J. Am. Chem. Soc. 2018; 140: 1267
61 Feng J, Noack F, Krische MJ. J. Am. Chem. Soc. 2016; 138: 12364
62 Corden BB, Drago RS, Perito RP. J. Am. Chem. Soc. 1985; 107: 2903
63 Hamilton DE, Drago RS, Zombeck A. J. Am. Chem. Soc. 1987; 109: 374
64 Mukaiyama T, Yamada T. Bull. Chem. Soc. Jpn. 1995; 68: 17
65 Isayama S, Mukaiyama T. Chem. Lett. 1989; 18: 1071
66 Kim D, Rahaman SM. W, Mercado BQ, Poli R, Holland PL. J. Am. Chem. Soc. 2019; 141: 7473
67 Lo JC, Kim D, Pan CM, Edwards JT, Yabe Y, Gui J, Qin T, Gutiérrez S, Giacoboni J, Smith MW, Holland PL, Baran PS. J. Am. Chem. Soc. 2017; 139: 2484
68 Gui J, Pan CM, Jin Y, Qin T, Lo JC, Lee BJ, Spergel SH, Mertzman ME, Pitts WJ, La Cruz TE, Schmidt MA, Darvatkar N, Natarajan SR, Baran PS. Science 2015; 348: 886
69 Cole SJ, Kirwan JN, Roberts BP, Willis CR. J. Chem. Soc., Perkin Trans. 1 1991; 103
70 Armstrong DA, Sun Q, Schuler RH. J. Phys. Chem. 1996; 100: 9892
71 Dénès F, Pichowicz M, Povie G, Renaud P. Chem. Rev. 2014; 114: 2587
72 Whittemore SM, Autrey T. Isr. J. Chem. 2015; 55: 196