Dehydrative Cross-Coupling of 1-Phenylethanol Catalysed by Palladium Nanoparticles Formed in situ Under Acidic Conditions

Jason E. Camp; Thomas W. Bousfield; Jay J. Dunsford; James Adams; Joshua Britton; Michael W. Fay; Athanasios Angelis-Dimakis

doi:10.1055/s-0037-1610246

Synthesis, Table of Contents

Synthesis 2018; 50(19): 3862-3874
DOI: 10.1055/s-0037-1610246

feature

Dehydrative Cross-Coupling of 1-Phenylethanol Catalysed by Palladium Nanoparticles Formed in situ Under Acidic Conditions

Jason E. Camp *

^aSchool of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK

^cDepartment of Chemical Sciences, University of Huddersfield, Queensgate, Huddersfield, HD1 3DH, UK

,

Thomas W. Bousfield

^cDepartment of Chemical Sciences, University of Huddersfield, Queensgate, Huddersfield, HD1 3DH, UK

,

Jay J. Dunsford

^aSchool of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK

,

James Adams

^aSchool of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK

,

Joshua Britton

^aSchool of Chemistry, University of Nottingham, Nottingham, NG7 2RD, UK

,

Michael W. Fay

^bNottingham Nanotechnology and Nanoscience Centre, University of Nottingham, Nottingham, NG7 2RD, UK

,

Athanasios Angelis-Dimakis

^cDepartment of Chemical Sciences, University of Huddersfield, Queensgate, Huddersfield, HD1 3DH, UK

› Author Affiliations

Abstract

All articles of this category

Abstract

A dehydrative cross-coupling of 1-phenylethanol catalysed by sugar derived, in situ formed palladium(0) nanoparticles under acidic conditions is realised. The acidic conditions allow for use of alcohols as a feedstock in metal-mediated coupling reactions via their in situ dehydration and subsequent cross-coupling. Extensive analysis of the size and morphology of the palladium nanoparticles formed in situ showed that the zero-valent metal was surrounded by hydrophilic hydroxyl groups. EDX-TEM imaging studies using a prototype silicon drift detector provided insight into the problematic role of molecular oxygen in the system. This increased understanding of the catalyst deactivation allowed for the development of the cross-coupling methodology. A 250-12,000 fold increase in molar efficiency was observed when compared to related two-step protocols that use alternative feedstocks for the palladium-mediated synthesis of stilbenes. This work opens up a new research area in which the active catalyst is formed, stabilised and regenerated by a renewable sugar.

Key words

glucose - nanoparticles - catalysis - dehydrative heck - palladium

Full Text

References

References

For recent examples, see:

1a Cheng G. Wang P. Yu J.-Q. Angew. Chem. Int. Ed. 2017; 56: 8183
1b Bao X. Wang Q. Zhu J. Angew. Chem. Int. Ed. 2017; 56: 9577
1c Qi X. Chen P. Liu G. Angew. Chem. Int. Ed. 2017; 56: 9517

2a Heck RF. Acc. Chem. Res. 1979; 12: 146
2b Dounay AB. Overman LE. Chem. Rev. 2003; 103: 2945

3a Czaplik WM. Mayer M. Cvengros J. von Wangelin AJ. ChemSusChem 2009; 2: 396
3b McGuinness DS. Cavell KJ. Skelton BW. White AH. Organometallics 1999; 18: 1596
3c Yin L. Liebscher J. Chem. Rev. 2007; 107: 133
3d Beletskaya IP. Cheprakov AV. Coord. Chem. Rev. 2004; 248: 2337

4a Dupont J. de Souza RF. Suares PA. Z. Chem. Rev. 2002; 102: 3667
4b Li C.-J. Chem. Rev. 2005; 105: 3095
4c Lamblin M. Nassar-Hardy L. Hierso J.-C. Fouquet E. Felpin F.-X. Adv. Synth. Catal. 2010; 352: 33

5a Kappe CO. Angew. Chem. Int. Ed. 2004; 43: 6250
5b Fu GC. Acc. Chem. Res. 2008; 41: 1555
5c Carmichael AJ. Earle MJ. Holbrey JD. McCormac PB. Sneddon KR. Org. Lett. 1999; 1: 997
5d Deshmukh RR. Rajagopal R. Srinivasan KV. Chem. Commun. 2001; 1544

6a Taylor JG. Moro AV. Correia CR. D. Eur. J. Org. Chem. 2011; 1403
6b Beletskaya IP. Cheprakov AV. Chem. Rev. 2000; 100: 3009

7a Li Z. Gelbaum C. Fisk JS. Holden B. Jaganathan A. Whiteker GT. Pollet P. Liotta CL. J. Org. Chem. 2016; 81: 8520
7b Kantam ML. Reddy PV. Srinivas P. Bhargava S. Tetrahedron Lett. 2011; 52: 4490

8a Saiyed AS. Bedekar AV. Tetrahedron Lett. 2010; 51: 6227
8b Meng G. Szostak M. Angew. Chem. Int. Ed. 2015; 54: 14518

9 Ruan J. Li X. Saidi O. Xiao J. J. Am. Chem. Soc. 2008; 130: 2424
10 For a related example of dehalogenative cross-coupling, see: Jha AK. Kishor S. Jain N. RSC Adv. 2015; 5: 55218
11 Colbon P. Barnard JH. Purdie M. Mulholland K. Kozhevnikoc I. Xiao J. Adv. Synth. Catal. 2012; 354: 1395
12 For the dehydration of aryl alcohols in Mizoroki–Heck reactions in ionic liquids, see: Kumar R. Shard A. Bharti R. Thopate Y. Sinha AK. Angew. Chem. Int. Ed. 2012; 51: 2636
13 Shad A. Rawat K. Sinha AK. Padwad Y. Kumar D. Eur. J. Org. Chem. 2016; 5941
14 Andhare NH. Thopate Y. Shamsuzzama Kumar L. Sharma T. Siddiqi MI. Sinha AK. Nazir A. Tetrahedron 2018; 74: 1655
15 Buijink JK. F. Lange JP. Bos AN. R. Horton AD. Niele FG. M. In Mechanisms in Homogenous and Heterogeneous Epoxidation Catalysts . Oyama ST. Elsevier; Amsterdam: 2008: 355
16 Cavani F. Trifiró F. Appl. Catal., A. 1995; 133: 219

17a Ward JK. Gardner JB. US Pat 4,161,554, 1979
17b Safe Handling and Storage of Styrene Monomer . Chevron Phillips Chemical Company LP,; 2010

18 Kogevinas M. Gwinn WM. Kriebel D. Phillips DH. Sim M. Bertke SJ. Calaf GM. Colosio C. Fritz JM. Fukushima S. Hemminki K. Jensen AA. Kolstad H. Mráz J. Nesnow S. Nylander-French LA. Parent ME. Sandy M. Smith-Roe SL. Stoner G. Suzuki T. Teixeira JP. Vodicka P. Tornero-Velez R. Guyton KZ. Grosse Y. El Ghissassi F. Bouvard V. Benbrahim-Tallaa L. Guha N. Vilahur N. Driscoll T. Hall A. Middleton D. Jaillet C. Mattock H. Straif K. Lancet Oncol. 2018;

19a Camp JE. Dunsford JJ. Cannons EP. Restorick WJ. Gadzhieva A. Fay MW. Smith RJ. ACS Sustainable Chem. Eng. 2014; 2: 500
19b Monopoli A. Calò V. Ciminale F. Cotugno P. Angelici C. Cioffi N. Nacci A. J. Org. Chem. 2010; 75: 3908

20 For a review, see: Kyne S. Camp JE. ACS Sustainable Chem. Eng. 2017; 5: 41
21 Camp JE. Dunsford JJ. Dacosta OS. G. Blundell RK. Adams J. Britton J. Smith RJ. Bousfield TW. Fay MK. RSC Adv. 2016; 6: 16115
22 Stahl SS. Science 2005; 309: 1824
23 See the Supporting Information for full details.
24 Ruan J. Xiao J. Acc. Chem. Res. 2011; 44: 614

25a Qin L. Ren X. Lu Y. Li Y. Zhou J. Angew. Chem. Int. Ed. 2012; 51: 5915
25b Qin L. Hirao H. Zhou J. Chem. Commun. 2012; 10236

26 McGonagle FI. Sneddon HF. Jamieson C. Watson AJ. B. ACS Sustainable Chem. Eng. 2014; 2: 523

For recent examples of Mol. E% calculations, see:

27a Malferrari D. Armenise N. Decesari S. Galletti P. Tagiavini E. ACS Sustainable Chem. Eng. 2015; 3: 1579
27b Agrawal NR. Bahekar SP. Sarode PB. Zade SS. Chandak HS. RSC Adv. 2015; 5: 47053
27c Reid BT. Reed SM. Green Chem. 2016; 18: 4263
27d Mistry L. Mapesa K. Bousfield TW. Camp JE. Green Chem. 2017; 19: 2123

28 Rohilla S. Pant P. Jain N. RSC Adv. 2015; 5: 31311
29 Littke AF. Fu GC. J. Am. Chem. Soc. 2001; 123: 6989

30a Comotti M. Pella CD. Falletta E. Rossi M. Adv. Synth. Catal. 2006; 348: 313
30b Panigrahi S. Kundu S. Ghosh SK. Nath S. Pal T. Colloids Surf. A 2005; 264: 133

31 Abbadi A. van Bekkum H. J. Mol. Catal. A: Chem. 1995; 97: 111
32 Rich PR. Biochem. Soc. Trans. 2003; 31: 1095
33 Reetz MT. Westermann E. Angew. Chem. Int. Ed. 2000; 39: 165
34 Fujimori K. Aust. J. Chem. 1977; 30: 685
35 Filipe V. Hawe A. Jiskoot J. Pharm. Res. 2010; 27: 796
36 Schätzel K. Drewel M. Ahrens J. J. Phys.: Condens. Matter 1990; 2: SA393
37 Roberts GS. Kozak D. Anderson W. Broom MF. Vogel R. Trau M. Small 2010; 6: 2653
38 Peng Z.-Y. Ma F.-F. Zhu L.-F. Xie X.-M. Zhang Z. J. Org. Chem. 2009; 74: 6855
39 Ganapathy D. Sekar G. Org. Lett. 2014; 16: 3856
40 Fu S. Chen N.-Y. Liu X. Shao Z. Luo S.-P. Liu Q. J. Am. Chem. Soc. 2016; 138: 8588
41 Lei C. Yip YJ. Zhou JS. J. Am. Chem. Soc. 2017; 139: 6086
42 Niwa T. Nakada M. J. Am. Chem. Soc. 2012; 134: 13538
43 Tang J. Hackenberger D. Goossen LJ. Angew. Chem. Int. Ed. 2016; 55: 11296
44 Cahiez G. Gager O. Lecomte F. Org. Lett. 2008; 10: 5255
45 Agasti S. Dey A. Maiti D. Chem. Commun. 2016; 12191
46 Yu J.-Y. Shimizu R. Kuwano R. Angew. Chem. Int. Ed. 2010; 49: 6396
47 Alacid E. Nájera C. J. Org. Chem. 2008; 73: 2315
48 Zhong J.-J. Liu Q. Wu C.-J. Meng Q.-Y. Gao X.-W. Li Z.-J. Chen B. Tung C.-H. Wu L.-Z. Chem. Commun. 2016; 1800
49 Gonzalez-de-Castro A. Xiao J. J. Am. Chem. Soc. 2015; 137: 8206
50 Hansmann MH. López-Andarias A. Rettenmeier E. Egler-Lucas C. Rominger F. Hashmi AS. L. Romero-Nieto C. Angew. Chem. Int. Ed. 2016; 55: 1196
51 Wu G. Zhao X. Ji W. Zhang Y. Wang J. Chem. Commun. 2016; 1961
52 Sore HF. Blackwell DT. MacDonald SJ. Spring DR. Org. Lett. 2010; 12: 2806

Supplementary Material

Supporting Information