Highly efficient nickel/phosphine catalyzed cross-couplings of diarylborinic acids with aryl tosylates and sulfamates

Science China Chemistry

Volumn 57, Issue 8, 2014, Pages 1126-1131

  Ke, Haihua ^a   Chen, Xiaofeng ^a   Feng, Yuanyuan ^a   Zou, Gang ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

aryl sulfamate; aryl tosylate; cross coupling; diarylborinic acid; nickel; phosphine

Indexed keywords

CATALYSIS; CATALYSTS; COUPLINGS; NICKEL; PHOSPHORUS COMPOUNDS;

ARYL TOSYLATE; ARYLBORONIC ACIDS; CATALYST LOADINGS; CROSS-COUPLINGS; NICKEL CATALYST; PHOSPHINE; SULFAMATES; SUZUKI COUPLINGS;

SULFUR COMPOUNDS;

EID: 84905870618     PISSN: 16747291     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11426-014-5138-3     Document Type: Article

References (59)

1. Hall DG. Boronic Acids: Preparation, Applications in Organic Synthesis and Medicine. 2nd ed. Weinheim: Willey-VCH, 2011
2. Suzuki A. Cross-coupling reactions of organoboranes: an easy way to construct C-C bonds (Nobel lecture). Angew Chem Int Ed, 2011, 50: 6722-6737
3. Johansson Seechurn CCC, Kitching MO, Colacot TJ, Snieckus V. Palladium-catalyzed cross-coupling: a historical contextual perspective to the 2010 Nobel prize. Angew Chem Int Ed, 2012, 51: 5062-5085
4. Percec V, Bae JY, Hill DH. Aryl mesylates in metal catalyzed homocoupling and cross-coupling reactions. 2. Suzuki-type nickel-catalyzed cross-coupling of aryl arenesulfonates and aryl mesylates with arylboronic acids. J Org Chem, 1995, 60: 1060-1065
5. Goossen LJ, Goossen K, Stanciu C. C(aryl)-O activation of aryl carboxylates in nickel-catalyzed biaryl syntheses. Angew Chem Int Ed, 2009, 48: 3569-3571
6. Rosen BM, Quasdorf KW, Wilson DA, Zhang N, Resmerita AM, Garg NK, Percec V. Nickel-catalyzed cross-couplings involving carbon-oxygen bonds. Chem Rev, 2011, 111: 1346-1416
7. Jana R, Pathak TP, Sigman MS. Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners. Chem Rev, 2011, 111: 1417-1492
8. Leowanawat P, Zhang N, Percec V. Nickel catalyzed cross-coupling of aryl C-O based electrophiles with aryl neopentylglycol boronates. J Org Chem, 2012, 77: 1018-1025
9. Yamaguchi J, Muto K, Itami K. Recent progress in nickel-catalyzed biaryl coupling. Eur J Org Chem, 2013: 19-30
10. Han FS. Transitionmetal-catalyzed Suzuki-Miyaura cross-coupling reactions: a remarkable advance from palladium to nickel catalysts. Chem Soc Rev, 2013, 42: 5270-5298
11. g). Org Biomol Chem, 2008, 6: 19-25 (Pubitemid 350255955)
12. Tang ZY, Hu QS. Room-temperature Ni(0)-catalyzed cross-coupling reactions of aryl arenesulfonates with arylboronic acids. J Am Chem Soc, 2004, 126: 3058-3059 (Pubitemid 38380705)
13. 2(dppe)- catalyzed cross-coupling of aryl mesylates, arenesulfonates, and halides with arylboronic acids. J Org Chem, 2004, 69: 3447-3452 (Pubitemid 38621293)
14. Molander GA, Beaumard F. Nickel-catalyzed C-O activation of phenol derivatives with potassium heteroaryl trifluoroborates. Org Lett, 2010, 12: 4022-4025
15. Guan BT, Lu XY, Zheng Y, Yu DG, Wu T, Li KL, Li BJ, Shi ZJ. Biaryl construction through Kumada coupling with diarylsulfates as one-by-one electrophiles under mild conditions. Org Lett, 2010, 12: 396-399
16. 3 catalyzed cross-coupling of aryl and heteroaryl neopentylglycol boronates with aryl and heteroaryl mesylates and sulfamates in THF at room temperature. J Org Chem, 2011, 76: 9946-9955
17. Fan XH, Yang LM. Room-temperature nickel-catalysed Suzuki-Miyaura reactions of arylsulfonates/halides with arylboronic acids. Eur J Org Chem, 2011: 1467-1471
18. 2]-catalyzed cross-coupling reactions of aryl/alkenyl sulfonates with arylboronic acids. Adv Synth Catal, 2011, 353: 2051-2059
19. 3 catalyzed cross-coupling of aryl and heteroaryl neopentylglycol boronates with aryl and heteroaryl mesylates and sulfamates at room temperature. J Org Chem, 2012, 77: 2885-2892
20. 2: a simple and efficient catalyst precursor for the Suzuki cross-coupling of aryl tosylates and aryl boronic acids. Org Lett, 2001, 3: 3049-3051 (Pubitemid 33625325)
21. Quasdorf KW, Tian X, Garg NK. Cross-coupling reactions of aryl pivalates with boronic acids. J Am Chem Soc, 2008, 130: 14422-14423
22. Guan BT, Wang Y, Li BJ, Yu DG, Shi ZJ. Biaryl construction via Ni-catalyzed C-O activation of phenolic carboxylates. J Am Chem Soc, 2008, 130: 14468-14470
23. Quasdorf KW, Riener M, Petrova KV, Garg NK. Suzuki-Miyaura coupling of aryl carbamates, carbonates, and sulfamates. J Am Chem Soc, 2009, 131: 17748-17749
24. Baghbanzadeh M, Pilger C, Kappe CO. Rapid nickel-catalyzed Suzuki-Miyaura cross-couplings of aryl carbamates and sulfamates utilizing microwave heating. J Org Chem, 2011, 76: 1507-1510
25. Quasdorf KW, Antoft-Finch A, Liu P, Silberstein AL, Komaromi A, Blackburn T, Ramgren SD, Houk KN, Snieckus V, Garg NK. Suzuki-Miyaura cross-coupling of aryl carbamates and sulfamates: experimental and computational studies. J Am Chem Soc, 2011, 133: 6352-6363
26. Antoft-Finch A, Blackburn T, Snieckus V. N,N-diethyl O-carbamate: directed metalation group and orthogonal Suzuki-Miyaura cross-coupling partner. J Am Chem Soc, 2009, 131: 17750-17752
27. Xu L, Li BJ, Wu ZH, Lu XY, Guan BT, Wang BQ, Zhao KQ, Shi ZJ. Nickel-catalyzed efficient and practical Suzuki-Miyaura coupling of alkenyl and aryl carbamates with arylboroxines. Org Lett, 2010, 12: 884-887
28. Chen H, Huang Z, Hu X, Tang G, Xu P, Zhao Y, Cheng CH. Nickel-catalyzed cross-coupling of aryl phosphates with arylboronic acids. J Org Chem, 2011, 76: 2338-2344
29. 2/dppp system (dppp = 1,3-bis(diphenylphosphino)propane). Chem Eur J, 2010, 16: 4991-4994
30. Chen GJ, Huang J, Gao LX, Han FS. Nickel-catalyzed cross-coupling of phenols and arylboronic acids through an in situ phenol activation mediated by PyBroP. Chem Eur J, 2011, 17: 4038-4042
31. Tobisu M, Shimasaki T, Chatani N. Nickel-catalyzed cross-coupling of aryl methyl ethers with arylboronic esters. Angew Chem Int Ed, 2008, 47: 4866-4869
32. Li XJ, Zhang JL, Geng Y, Jin Z. Nickel-catalyzed Suzuki-Miyaura coupling of heteroaryl ethers with arylboronic acids. J Org Chem, 2013, 78: 5078-5084
33. 2 C-O bond of naphtholate. Angew Chem Int Ed, 2011, 50: 7097-7100
34. Lundin PM, Fu GC. Asymmetric Suzuki cross-couplings of activated secondary alkyl electrophiles: arylations of racemic a-chloroamides. J Am Chem Soc, 2010, 132: 11027-11029
35. Owston NA, Fu GC. Asymmetric alkyl-alkyl cross-couplings of unactivated secondary alkyl electrophiles: stereoconvergent Suzuki reactions of racemic acylated halohydrins. J Am Chem Soc, 2010, 132: 11908-11909
36. Zultanski SL, Fu GC. Catalytic asymmetric Γ-alkylation of carbonyl compounds via stereoconvergent Suzuki cross-couplings. J Am Chem Soc, 2011, 133: 15362-15364
37. Lu Z, Wilsily A, Fu GC. Stereoconvergent amine-directed alkyl-alkyl Suzuki reactions of unactivated secondary alkyl chlorides. J Am Chem Soc, 2011, 133: 8154-8157
38. Wilsily A, Tramutola F, Owston NA, Fu GC. New directing groups for metal-catalyzed asymmetric carbon-carbon bond-forming processes: stereoconvergent alkyl-alkyl Suzuki cross-couplings of unactivated electrophiles. J Am Chem Soc, 2012, 134: 5794-5797
39. Zultanski SL, Fu GC. Nickel-catalyzed carbon-carbon bond-forming reactions of unactivated tertiary alkyl halides: Suzuki arylations. J Am Chem Soc, 2013, 135: 624-627
40. Partyka DV. Transmetalation of unsaturated carbon nucleophiles from boron-containing species to the mid to late d-block metals of relevance to catalytic C-X coupling reactions (X = C, F, N, O, Pb, S, Se, Te). Chem Rev, 2011, 111: 1529-1595
41. Ito T, Iwai T, Mizuno T, Ishino Y. Palladium-catalyzed cross-coupling reaction of potassium diaryldifluoroborates with aryl halides. Synlett, 2003, 10: 1435-1438 (Pubitemid 36986576)
42. Winkle DD, Schaab KM. Suzuki reaction of a diarylborinic acid: one-pot preparation and cross-coupling of bis(3,5-dimethylphenyl)borinic acid. Org Process Res Dev, 2001, 5: 450-451
43. Haag BA, Sämann C, Jana A, Knochel P. Practical one-pot preparation of magnesium di(hetero)aryl- and magnesium dialkenylboronates for Suzuki-Miyaura cross-coupling reactions. Angew Chem Int Ed, 2011, 50: 7290-7294
44. Li X, Feng Y, Lin L, Zou G. Synthesis of diarylmethanes via metal-free reductive cross-coupling of diarylborinic acids with tosylhydrazones. J Org Chem, 2012, 77: 10991-10995
45. Chen X, Ke H, Chen Y, Guan C, Zou G. Cross-coupling of diarylborinic acids and anhydrides with arylhalides catalyzed by a phosphite/ N-heterocyclic carbene co-supported palladium catalyst system. J Org Chem, 2012, 77: 7572-7578
46. Cole TE, Haly BD. Selective preparation of borinic esters from Grignard reagents and selected trialkoxyboranes. Organometallics, 1992, 11: 652-657
47. Brown HC, Racherla US. Organoboranes. 43. A convenient, highly efficient synthesis of triorganylboranes via a modified organometallic route. J Org Chem, 1986, 51: 427-432
48. Huang SW, Shan ZX, Zhao DJ. A simple and convenient preparation of aryl boronic and diarylborinic acids by one-pot Grignard reaction. Chin J Org Chem, 1995, 15: 64-67
49. Turner WR, Elving PJ. Electrooxidation of tetraphenylborate ion at the pyrolytic graphite electrode. Anal Chem, 1965, 37: 207-211
50. Geske DH. The electrooxidation of the tetraphenylborate ion: an example of a secondary chemical reaction following the primary electrode process. J Phys Chem, 1959, 63: 1062-1070
51. Chen X, Ke H, Zou G. Nickel-catalyzed cross-coupling of diarylborinic acids with aryl chlorides. ACS Catal, 2014, 4: 379-385
52. Mesganaw T, Garg NK. Ni- and Fe-catalyzed cross-coupling reactions of phenol derivatives. Org Process Res Dev, 2013, 17: 29-39
53. Rappoport Z. The Chemistry of Phenols. Chichester: John Wiley & Sons, 2003
54. Van Hecke GR, Horrocks Jr WD. Ditertaryphosphine complexes of nickel: spectral, magnetic, and proton resonance studies. A planartetrahedral equilibrium. Inorg Chem, 1966, 5: 1968-1974
55. Rudie AW, Lichtenberg DW, Katcher ML, Davison A. Comparative study of 1,l′-bis(dipheny1phosphino)cobalt ocenium hexafluorophosphate and 1,l′-bis(dipheny1phosphino)ferrocene as bidentate ligands. Inorg Chem, 1978, 17: 2859-2863
56. Browning MC, Davies RFB, Morgan DJ, Sutton LE, Venanzi LM. Tetrahedral nickel(II) complexes and the factors determining their formation. Part III. Complexes with triarylphosphines. J Chem Soc, 1961: 4816-4823
57. Ueda M, Saitoh A, Oh-tani S, Miyaura N. Synthesis of biaryls via nickel-catalyzed cross-coupling reaction of arylboronic acids and aryl mesylates. Tetrahedron, 1998, 54: 13079-13086 (Pubitemid 28470694)
58. 2] with only1 mol% loading. Adv Synth Catal, 2011, 353: 309-314
59. Dierkes P, Leeuwen PWNM. The bite angle makes the difference: a practical ligand parameter for diphosphine ligands. J Chem Soc, Dalton Trans, 1999: 1519-1529