Some recent advances in transition-metal-catalyzed ortho SP2 C-H functionalization using Ru, Rh, and Pd

Science China Chemistry

Volumn 57, Issue 7, 2014, Pages 930-944

  Rao, Yu ^a   Shan, Gang ^a   Yang, Xinglin ^a  

^a Tsinghua University   (China)

Author keywords

directing group; ortho selectivity; transition metal catalysis; weak coordination

Indexed keywords

ACTIVATION ANALYSIS; CATALYSIS; COORDINATION REACTIONS; FUNCTIONAL GROUPS; KETONES; RHODIUM; TRANSITION METALS;

C-H FUNCTIONALIZATION; DIRECTING GROUPS; ORTHO-SELECTIVITY; TRANSITION METAL CATALYSIS; WEAK COORDINATION;

RUTHENIUM;

EID: 84903704256     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-014-5130-y     Document Type: Review

References (77)

1. Kakiuchi F, Chatani N. Catalytic Methods for C-H bond functionalization: application in organic synthesis. Adv Synth Catal, 2003, 345: 1077-1101
2. Dick AR, Sanford MS. Transition metal catalyzed oxidative functionalization of carbon-hydrogen bonds. Tetrahedron, 2006, 62: 2439-2463
3. Godula K, Sames D. C-H bond functionalization in complex organic synthesis. Science, 2006, 312: 67-72
4. Yu JQ, Giri R, Chen X. σ-Chelation-directed C-H functionalizations using Pd(II) and Cu(II) catalysts: regioselectivity, stereoselectivity and catalytic turnover. Org Biomol Chem, 2006, 4: 4041-4047
5. Alberico D, Scott ME, Lautens M. Aryl-aryl bond formation by transition-metal-catalyzed direct arylation. Chem Rev, 2007, 107: 174-238
6. Ackermann L, Vicente R, Kapdi AR. Transition-metal-catalyzed direct arylation of (hetero)arenes by C-H bond cleavage. Angew Chem Int Ed, 2009, 48: 9792-9826
7. Daugulis O, Do HQ, Shabashov D. Palladium- and copper-catalyzed arylation of carbon-hydrogen bonds. Acc Chem Res, 2009, 42: 1074-1086
8. Colby DA, Bergman RG, Ellman JA. Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation. Chem Rev, 2010, 110: 624-655
9. Lyons TW, Sanford MS. Palladium-catalyzed ligand-directed C-H functionalization reactions. Chem Rev, 2010, 110: 1147-1169
10. Xu LM, Li BJ, Yang Z, Shi ZJ. Organopalladium(IV) chemistry. Chem Soc Rev, 2010, 39: 712-733
11. Ackermann L, Vicente R, Kapdi AR. Carboxylate-assisted transition-metalcatalyzed C-H bond functionalizations: mechanism and scope. Chem Rev, 2011, 111: 1315-1345
12. Colby DA, Tsai AS, Bergman RG, Ellman JA. Rhodium catalyzed chelation-assisted C-H bond functionalization reactions. Acc Chem Res, 2012, 45: 814-825
13. Neufeldt SR, Sanford MS. Controlling site selectivity in palladium-catalyzed C-H bond functionalization. Acc Chem Res, 2012, 45: 936-946
14. Yu DG, Li BJ, Shi ZJ. Challenges in C-C bond formation through direct transformations of sp2 C-H bonds. Tetrahedron, 2012, 68: 5130-5136
15. Yan GB, Wu XM, Yang MH. Transition-metal-catalyzed additions of C-H bonds to C-X (X = N, O) multiple bonds via C-H bond activation. Org Biomol Chem, 2013, 11: 5558-5578
16. Zheng QZ, Jiao N. Transition-metal-catalyzed ketonedirected ortho-C-H functionalization reactions. Tetrahedron Lett, 2014, 55: 1121-1126
17. Engle KM, Mei TS, Wasa M, Yu JQ. Weak coordination as a powerful means for developing broadly useful C-H functionalization reactions. Acc Chem Res, 2012, 45: 788-802
18. Murai S, Kakiuchi F, Sekine S, Tanaka Y, Kamatani A, Sonoda M, Chatani N. Efficient catalytic addition of aromatic carbon-hydrogen bonds to olefins. Nature, 1993, 366: 529-531
19. Kakiuchi F, Yamamoto Y, Chatani N, Murai S. Catalytic addition of aromatic C-H bonds to acetylenes. Chem Lett, 1995, 8: 681-682
20. Kakiuchi F, Kan S, Igi K, Chatani N, Murai S. A ruthenium-catalyzed reaction of aromatic ketones with arylboronates: a new method for the arylation of aromatic compounds via C-H bond cleavage. J Am Chem Soc, 2003, 125: 1698-1699
21. Martinez R, Chevalier R, Darses S, Genet JP. A versatile ruthenium catalyst for C-C bond Formation by C-H bond activation. Angew Chem Int Ed, 2006, 45: 8232-8235
22. Martinez R, Simon MO, Chevalier R, Pautigny C, Genet JP, Darses S. C-C bond formation via C-H bond activation using an in situ-generated ruthenium catalyst. J Am Chem Soc, 2009, 131: 7887-7895
23. Thirunavukkarasu VS, Ackermann L. Ruthenium-catalyzed C-H bond oxygenations with weakly coordinating ketones. Org Lett, 2012, 14, 6206-209
24. Shan G, Han XS, You SY, Lin Y, Rao Y. Broadening the catalyst and reaction scope of regio- and chemoselective C-H oxygenation: a convenient and scalable approach to 2-acylphenols by intriguing Rh(II) and Ru(II) catalysis. Org Biomol Chem, 2013, 1: 2318-2322
25. Kim J, Kim J, Chang S. Ruthenium-catalyzed direct C-H amidation of arenes including weakly coordinating aromatic ketones. Chem Eur J, 2013, 19: 7328-7333
26. Zheng QZ, Liang YF, Qin C, Jiao N. Ru(II)-catalyzed intermolecular C-H amidation of weakly coordinating ketones. Chem Commun, 2013, 49: 5654-5656
27. Bhanuchandra M, Yadav MR, Rit RK, Kuram MR, Sahoo A. Ru(II)-catalyzed intermolecular ortho-C-H amidation of aromatic ketones with sulfonyl azides. Chem Commun, 2013, 49: 5225-5257
28. Sonoda M, Kakiuchi F, Kamatani A, Chatani N, Murai S. Ruthenium-catalyzed addition of aromatic esters at the ortho C-H Bonds to olefins. Chem Lett, 1996, 109-110
29. 3-catalyzed addition of C-H bonds in aromatic esters to olefin. Chem Lett, 2001: 918-919
30. Nishimura T, Washitake Y, Uemura S. Ruthenium/halide catalytic system for C-C bond forming reaction between alkynes and unsaturated carbonyl compounds. Adv Synth Catal, 2007, 349: 2563-2571
31. Neisius NM, Plietker B. The ruthenium-catalyzed hydrovinylation of internal alkynes by acrylates: an atom economic approach to highly substituted 1,3-dienes. Angew Chem Int Ed, 2009, 48:5752-5755
32. Graczyk K, Ma W, Ackermann L. Oxidative alkenylation of aromatic esters by ruthenium-catalyzed twofold C-H bond cleavages. Org Lett, 2012, 14: 4110-4113
33. Yang YQ, Lin Y, Rao Y. Ruthenium(II)-catalyzed synthesis of hydroxylated arenes with ester as an effective directing group. Org Lett, 2012, 14: 2874-2877
34. Li B, Ma JF, Liang Y, Wang NC, Xu SS, Song H, Wang BQ. Regio- and stereoselective olefination of phenol carbamates through C-H bond functionalization. Eur J Org Chem, 2013: 1950-1962
35. Reddy MC, Jeganmohan M. Ruthenium-catalyzed selective aerobic oxidative ortho-alkenylation of substituted phenols with alkenes through C-H bond activation. Eur J Org Chem, 2013: 1150-1157
36. 2)-H oxygenations of phenol derivatives. Org Lett, 2013, 15: 3484-3486
37. 2)-H bond hydroxylation: site-selective C-O bond formation on benzamides. Org Lett, 2012, 14: 4210-4213
38. Yang F, Ackermann L. Ruthenium-catalyzed C-H oxygenation on aryl weinreb amides. Org Lett, 2013, 15: 718-720
39. Yang XL, Shan G, Rao Y. Synthesis of 2-aminophenols and heterocycles by Ru-catalyzed C-H mono- and dihydroxylation. Org Lett, 2013, 15: 2334-2337
40. Muralirajan K, Parthasarathy K, Cheng CH. Regioselective synthesis of indenols by rhodium-catalyzed C-H activation and carbocyclization of aryl ketones and alkynes. Angew Chem Int Ed, 2011, 50, 4169-4172
41. Patureau FW, Besset T, Kuhl N, Glorius F. Diverse strategies toward indenol and fulvene derivatives: Rh-catalyzed C-H activation of aryl ketones followed by coupling with internal alkynes. J Am Chem Soc, 2011, 133: 2154-2156
42. Wencel-Delord J, Nimphius C, Wang H, Glorius F. Rhodium(III) and hexabromobenzene: a catalyst system for the cross-dehydrogenative coupling of simple arenes and heterocycles with arenes bearing directing groups. Angew Chem Int Ed, 2012, 51: 13001-13005
43. Shi XY, Li CJ. Synthesis of indene frameworks via rhodium-catalyzed cascade cyclization of aromatic ketone and unsaturated carbonyl compounds. Org Lett, 2013, 15: 1476-1479
44. Shin K, Baek Y, Chang S. Direct C-H amination of arenes with alkyl azides under rhodium catalysis. Angew Chem Int Ed. 2013, 52: 8031-8036
45. Schroder N, Wencel-Delord J, Glorius F. High-yielding, versatile, and practical [Rh(III)Cp]-catalyzed ortho bromination and iodination of arenes. J Am Chem Soc, 2012, 134: 8298-8301
46. Park SH, Kim JY, Chang S. Rhodium-catalyzed selective olefination of arene esters via C-H bond activation. Org Lett, 2011, 13: 2372-2375
47. Gong TJ, Xiao B, Liu ZJ, Wan, Xu J, Luo DF, Fu Y, Liu L. Rhodium-catalyzed selective C-H activation/olefination of phenol carbamates. Org Lett, 2011, 13: 3235-3237
48. Feng C, Loh TP. Rhodium-catalyzed direct ortho C-H olefination of phenol derivatives. Chem Commun 2011, 47: 10458-10460
49. Zhang Q, Yu HZ, Li YT, Liu L, Huang Y, Fu Y. Computational study on mechanism of Rh(III)-catalyzed oxidative Heck coupling of phenol carbamates with alkenes. Dalton Trans, 2013, 42: 4175-4184
50. Yu M, Xie YJ, Xie CS, Zhang YH. Palladium-catalyzed C-H alkenylation of arenes using thioethers as directing groups. Org Lett, 2012, 14: 2164-2167
51. Yao JZ, Yu M, Zhang YH. Thioethers as directing group for the palladium-catalyzed direct arylation of arenes. Adv Synth Catal, 2012, 354, 3205-3210
52. Samanta r, Antonchick AP. Palladium-catalyzed double C-H activation directed by sulfoxides in the synthesis of dibenzothiophenes. Angew Chem Int Ed, 2011, 50: 5217-5220
53. Zhang XS, Zhu QL, Zhang YF, Li YB, Shi ZJ. Controllable mono-/dialkenylation of benzyl thioethers through Rh-catalyzed aryl C-H activation. Chem Eur J, 2013, 19: 11898-111903
54. Satoh T, Kametani Y, Terao Y, Miura M, Namura M. Palladium-catalyzed multiple arylation of phenyl ketones with aryl bromides. Tetrahedron Lett, 1999, 40: 5345-5348
55. Gandeepan P, Parthasarathy K, Cheng CH. Synthesis of phenanthrone derivatives from sec-alkyl aryl ketones and aryl halides via a palladium-catalyzed dual C-H bond activation and enolate cyclization. J Am Chem Soc, 2010, 132: 8569-8571
56. Xiao B, Gong TJ, Xu J, Liu ZJ, Liu L. Palladium-catalyzed intermolecular directed C-H amidation of aromatic ketones. J Am Chem Soc, 2011, 133: 1466-1474
57. Gandeepan P, Hung CH, Cheng CH. Pd-catalyzed double C-H bond activation of diaryl ketones for the synthesis of fluorenones. Chem Commun, 2012, 48: 9379-9381
58. Li H, Zhu RY, Shi WJ, He KH, Shi ZJ. Synthesis of fluorenone derivatives through Pd-catalyzed dehydrogenative cyclization. Org Lett, 2012, 14: 4850-4853
59. Shan G, Yang XL, Ma LL, Rao Y. Pd-catalyzed C-H oxygenation with TFA/TFAA: expedient access to oxygen-containing heterocycles and late-stage drug modification. Angew Chem Int Ed, 2012, 51: 13070-13074
60. Mo FY, Trzepkowski LJ, Dong GB. Synthesis of ortho-acylphenols through the palladium-catalyzed ketone-directed hydroxylation of arenes. Angew Chem Int Ed, 2012, 51: 13075-13079
61. Choy PY, Kwong FY. Palladium-catalyzed ortho-CH-bond oxygenation of aromatic ketones. Org Lett, 2013, 15: 270-273
62. Sun XY, Shan G, Sun YH, Rao Y. Regio- and chemoselective C-H chlorination/bromination of electron-deficient arenes by weak coordination and study of relative directing-group abilities. Angew Chem Int Ed, 2013, 52: 4440-4444
63. Xiao B, Fu Y, Xu J, Gong TJ, Dai JJ, Yi J, Liu L. Pd(II)-catalyzed C-H activation/aryl-aryl coupling of phenol esters. J Am Chem Soc, 2010, 132: 468-469
64. Bedford RB, Webstera RL, Mitchellb CJ. Palladium-catalysed ortho-arylation of carbamate-protected phenols. Org Biomol Chem, 2009, 7: 4853-4857
65. Zhao XD, Yeung CS, Dong VM. Palladium-catalyzed ortho-arylation of O-phenylcarbamates with simple arenes and sodium persulfate. J Am Chem Soc, 2010, 132: 5837
66. John A, Nicholas KM. Palladium catalyzed C-H functionalization of O-arylcarbamates: selective ortho-bromination using NBS. J Org Chem, 2012, 77: 5600-5605
67. Sun XY, Sun YH, Zhang C, Rao Y. Room-temperature Pd-catalyzed C-H chlorination by weak coordination: one-pot synthesis of 2-chlorophenols with excellent regioselectivity. Chem Commun, 2014, 50: 1262-1264
68. Lu Y, Wang DH, Engle KM, Yu JQ. Pd(II)-catalyzed hydroxyl-directed C-H olefination enabled by monoprotected amino acid ligands. J Am Chem Soc 2010, 132: 5916-5921
69. Wang X, Lu Y, Dai HX, Yu JQ. Pd(II)-catalyzed hydroxyl-directed C-H activation/C-O cyclization: expedient construction of dihydrobenzofurans. J Am Chem Soc, 2010, 132: 12203-12205
70. Wang H, Li G, Engle KM, Yu JQ, H. Davies ML. Sequential C-H functionalization reactions for the enantioselective synthesis of highly functionalized 2,3-dihydrobenzofurans. J Am Chem Soc, 2013, 135: 6774-6777
71. Chidipudi SR, Wieczysty MD, Khan I, Lam HW. Synthesis of benzopyrans by Pd(II)- or Ru(II)-catalyzed C-H alkenylation of 2-aryl-3-hydroxy-2- cyclohexenones. Org Lett, 2013, 15: 570-573
72. Xiao B, Gong TJ, Liu ZJ, Liu JH, Luo DF, Xu J, Liu L. Synthesis of dibenzofurans via palladium-catalyzed phenol-directed C-H activation/C-O cyclization. J Am Chem Soc, 2011, 133: 9250-9253
73. Lu Y, Leow D, Wang X, Engle KM, Yu JQ. Hydroxyl-directed C-H carbonylation enabled by mono-N-protected amino acid ligands: an expedient route to 1-isochromanones. Chem Sci, 2011, 2: 967-971
74. Huang A, Ghavtadze N, Chattopadhyay B, Gevorgyan V. Synthesis of catechols from phenols via pd-catalyzed silanol-directed C-H oxygenation. J Am Chem Soc, 2011, 133: 17630-1733
75. Li G, Leow D, Wan L, Yu JQ, Ether-directed ortho-C-H olefination with a palladium(II)/monoprotected amino acid catalyst. Angew Chem Int Ed, 2013, 52: 1245-1247
76. Gandeepan P, Cheng CH. Allylic carbon-carbon double bond directed Pd-catalyzed oxidative ortho-olefination of arenes. J Am Chem Soc, 2012, 134: 5738-5741
77. Minami Y, Shiraishi Y, Yamada K, Hiyama T. Palladium-catalyzed cycloaddition of alkynyl aryl ethers with internal alkynes via selective ortho C-H activation. J Am Chem Soc, 2012, 134: 6124-6127