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Flow Chemistry Syntheses of Styrenes, Unsymmetrical Stilbenes and Branched Aldehydes

Samuel L. Bourne¹,
Dr. Matthew O'Brien²,
Sivarajan Kasinathan³,
Dr. Peter Koos¹,
Dr. Päivi Tolstoy¹,
Dennis X. Hu¹,
Dr. Roderick W. Bates³,
Dr. Benjamin Martin⁴,
Dr. Berthold Schenkel⁴,
Prof. Steven V. Ley^1,*

Article first published online: 20 DEC 2012

DOI: 10.1002/cctc.201200778

Issue

ChemCatChem

Volume 5, Issue 1, pages 159–172, January 2013

Additional Information

How to Cite

Bourne, S. L., O'Brien, M., Kasinathan, S., Koos, P., Tolstoy, P., Hu, D. X., Bates, R. W., Martin, B., Schenkel, B. and Ley, S. V. (2013), Flow Chemistry Syntheses of Styrenes, Unsymmetrical Stilbenes and Branched Aldehydes. ChemCatChem, 5: 159–172. doi: 10.1002/cctc.201200778

Author Information

¹
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW (UK)
²
School of Physical & Geographical Sciences, Lennard-Jones Building, Keele University, Staffordshire, ST5 5BG (United Kingdom)
³
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, 637371 Singapore (Singapore)
⁴
Chemical & Analytical Development, Novartis Pharma AG, Werk Klybeck, Klybeckstr. 141, 4057 Basel (Switzerland)

Email: Prof. Steven V. Ley (svl1000@cam.ac.uk)

^*Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW (UK)

Publication History

Issue published online: 23 DEC 2012
Article first published online: 20 DEC 2012
Manuscript Received: 30 OCT 2012

Funded by

Novartis (S.L.B.)
Singapore Ministry of Education
Academic Research Fund Tier 1. Grant Number: RG 62/10
Astra Zeneca
Georganics Ltd
EPSRC. Grant Number: EP/F069685/1
BP 1702 Professorship

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1
1a
D. Webb, T. F. Jamison, Chem. Sci. 2010, 1, 675–680;
1b
R. L. Hartman, K. F. Jensen, Lab Chip 2009, 9, 2495–2507;
1c
B. P. Mason, K. E. Price, J. L. Steinbacher, A. R. Bogdan, D. T. McQuade, Chem. Rev. 2007, 107, 2300–2318;
1d
J. Wegner, S. Ceylan, A. Kirschning, Chem. Commun. 2011, 47, 4583–4592;
1e
C. Wiles, P. Watts, Chem. Commun. 2011, 47, 6512–6535;
1f
I. R. Baxendale, J. J. Hayward, S. Lanners, S. V. Ley, C. D. Smith, Microreactors in Organic Synthesis and Catalysis (Ed.: T. Wirth), Wiley, New York, 2008;
1g
J. Kobayashi, Y. Mori, K. Okamoto, R. Akiyama, M. Ueno, T. Kitamori, S. Kobayashi, Science 2004, 304, 1305–1308;
1h
J. I. Yoshida, Chem. Rec. 2010, 10, 332–341;
Direct Link:
1i
X. Y. Mak, P. Laurino, P. H. Seeberger, Beilstein J. Org. Chem. 2009, 5, 19;
1j
T. Razzaq, C. O. Kappe, Chem. Asian J. 2010, 5, 1274–1289;
- CAS,
- Web of Science® Times Cited: 77
1k
V. Hessel, Chem. Eng. Technol. 2009, 32, 1655–1681;
Direct Link:
1l
P. J. Nieuwland, K. Koch, N. van Harskamp, R. Wehrens, J. C. M. van Hest, F. Rutjes, Chem. Asian J. 2010, 5, 799–805;
Direct Link:
1m
B. Ahmed-Omer, J. C. Brandt, T. Wirth, Org. Biomol. Chem. 2007, 5, 733–740;
1n
R. D. Chambers, M. A. Fox, G. Sandford, J. Trmcic, A. Goeta, J. Fluorine Chem. 2007, 128, 29–33;
1o
T. Fukuyama, T. Rahman, N. Kamata, I. Ryu, Beilstein J. Org. Chem. 2009, 5, 34;
1p
P. W. Miller, L. E. Jennings, A. J. deMello, A. D. Gee, N. J. Long, R. Vilar, Adv. Synth. Catal. 2009, 351, 3260–3268.
Direct Link:
2
2a
B. M. Trost, Angew. Chem. 1995, 107, 285–307;
Direct Link:
Angew. Chem. Int. Ed. Engl. 1995, 34, 259–281;
Direct Link:
2b
P. Wender, Acc. Chem. Res. 2008, 41, 40–49;
2c
P. Wender, Organic Synthesis:Theory and Applications, Vol. 2 (Ed.: T. Hudlicky), JAI Press, Greenwich, 1993, pp. 27–66;
2d
S. V. Ley, Chem. Rec. 2012, 12, 378–390.
Direct Link:
3
3a
B. Gutmann, D. Obermayer, J. P. Roduit, D. M. Roberge, C. O. Kappe, J. Flow Chem. 2012, 2, 8–19;
3b
C. B. McPake, G. Sandford, Org. Process Res. Dev. 2012, 16, 844–851.
4
4a
D. L. Browne, M. Baumann, B. H. Harji, I. R. Baxendale, S. V. Ley, Org. Lett. 2011, 13, 3312–3315;
4b
A. Nagaki, E. Takizawa, J. Yoshida, Chem. Eur. J. 2010, 16, 14149–14158;
Direct Link:
4c
A. Nagaki, A. Kenmoku, Y. Moriwaki, A. Hayashi, J. Yoshida, Angew. Chem. 2010, 122, 7705–7709;
Direct Link:
Angew. Chem. Int. Ed. 2010, 49, 7543–7547.
Direct Link:
5
5a
D. L. Browne, B. J. Deadman, R. Ashe, I. R. Baxendale, S. V. Ley, Org. Process Res. Dev. 2011, 15, 693–697;
5b
C. B. Kelly, X. Lee, N. E. Leadbeater, Tetrahedron Lett. 2011, 52, 263–265;
5c
J. Sedelmeier, S. V. Ley, I. R. Baxendale, M. Baumann, Org. Lett. 2010, 12, 3618–3621;
5d
T. Horie, M. Sumino, T. Tanaka, Y. Matsushita, T. Ichimura, J. Yoshida, Org. Process Res. Dev. 2010, 14, 405–410;
5e
R. L. Hartman, J. R. Naber, N. Zaborenko, S. L. Buchwald, K. F. Jensen, Org. Process Res. Dev. 2010, 14, 1347–1357.
6
Purchased from Biogeneral Inc., 9925 Mesa Rim Road, San Diego, CA, USA. www.biogeneral.com.
7a
(CO₂) A. Polyzos, M. O’Brien, T. Pugaard-Petersen, I. R. Baxendale, S. V. Ley, Angew. Chem. 2011, 123, 1222–1225;
Direct Link:
Angew. Chem. Int. Ed. 2011, 50, 1190–1193;
Direct Link:
7b
(CO) P. Koos, U. Gross, A. Polyzos, M. O’Brien, I. R. Baxendale, S. V. Ley, Org. Biomol. Chem. 2011, 9, 6903–6908;
7c
(O₂) T. P. Petersen, A. Polyzos, M. O’Brien, T. Ulven, I. R. Baxendale, S. V. Ley, ChemSusChem 2012, 5, 274–277;
Direct Link:
7d
(O₃) M. O’Brien, I. R. Baxendale, S. V. Ley, Org. Lett. 2010, 12, 1596–1598;
7e
(H₂) M. O’Brien, N. Taylor, A. Polyzos, I. R. Baxendale, S. V. Ley, Chem. Sci. 2011, 2, 1250–1257;
7f
(H₂) S. Newton, S. V. Ley, E. Casas-Arce, D. M. Grainger, Adv. Synth. Catal. 2012, 354, 1805–1812;
Direct Link:
7g
(NH₃) D. L. Browne, M. O’Brien, P. Koos, P. B. Cranwell, A. Polyzos, S. V. Ley, Synlett 2012, 23, 1402–1406;
7h
(NH₃) P. B. Cranwell, M. O’Brien, D. L. Browne, P. Koos, A. Polyzos, M. Peña-López, S. V. Ley, Org. Biomol. Chem. 2012, 10, 5774–5779;
7i
(ethylene) S. L. Bourne, P. Koos, M. O’Brien, B. Martin, B. Schenkel, I. R. Baxendale, S. V. Ley, Synlett 2011, 18, 2643–2647;
7j
(syngas) S. Kasinathan, S. L. Bourne, P. Tolstoy, P. Koos, M. O’Brien, R. W. Bates, I. R. Baxendale, S. V. Ley, Synlett 2011, 18, 2648–2651.
8
T. Mizoroki, K. Mori, A. Ozaki, Chem. Soc. Jpn. 1971, 44, 581.
9
9a
R. F. Heck, J. P. Nolley, J. Org. Chem. 1972, 37, 2320–2322;
9b
R. F. Heck, J. Am. Chem. Soc. 1969, 91, 6707–6714;
9c
J. E. Plevyak, R. F. Heck, J. Org. Chem. 1978, 43, 2454–2456;
9d
A. H. M. de Vries, J. C. M. A. Mulders, J. H. M. Mommers, H. J. M. Henderick, J. G. de Vries, Org. Lett. 2003, 5, 3285–3288.
10
10a
B. Ahmed-Omer, D. A. Barrow, T. Wirth, Tetrahedron Lett. 2009, 50, 3352–3355;
10b
N. Nikbin, M. Ladlow, S. V. Ley, Org. Process Res. Dev. 2007, 11, 458–462.
11
11a
F. Kerins, D. F. J. O’Shea, J. Org. Chem. 2002, 67, 4968–4971;
11b
E. Peyroux, F. Berthiol, H. Doucet, M. Santelli, Eur. J. Org. Chem. 2004, 1075–1082;
Direct Link:
11c
S. Darses, G. Michaud, J.-P. Genet, Eur. J. Org. Chem. 1999, 1875–1883;
Direct Link:
11d
S. Darses, G. Michaud, J.-P. Genet, Tetrahedron Lett. 1998, 39, 5045–5048;
11e
S. K. Stewart, A. J. Whiting, Organomet. Chem. 1994, 482, 293–300;
11f
A. P. Lightfoot, S. J. R. Twiddle, A. Whiting, Synlett 2005, 529–531;
- CAS,
- Web of Science® Times Cited: 19
11g
G. A. Molander, M. R. Rivero, Org. Lett. 2002, 4, 107–109;
11h
G. A. Molander, A. R. Brown, J. Org. Chem. 2006, 71, 9681–9686.
12
12a
A. F. Littke, L. Schwartz, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 6343–6348;
12b
G. A. Grasa, S. P. Nolan, Org. Lett. 2001, 3, 119–122;
12c
D. R. McKean, G. Parrinello, A. F. Renaldo, J. K. Stille, J. Org. Chem. 1987, 52, 422–424;
12d
E. Shirakawa, K. Yamasaki, H. Tamerjiro, Synthesis 1998, 1544–1549;
- CrossRef,
- CAS
12e
M. E. Krolski, A. F. Renaldo, D. E. Rudisill, J. K. Stille, J. Org. Chem. 1988, 53, 1170–1176;
12f
V. Farina, S. Kapadia, B. Krishnan, C. Wang, L. S. Liebeskind, J. Org. Chem. 1994, 59, 5905–5911.
13
13a
C. M. Kormos, N. E. Leadbeater, J. Org. Chem. 2008, 73, 3854–3858;
13b
C. R. Smith, T. V. RajanBabu, Tetrahedron 2010, 66, 1102–1110;
13c
B. M. Bhanage, S.-I. Fujita, T. Yoshida, Y. Sano, M. Arai, Tetrahedron Lett. 2003, 44, 3505–3507;
13d
J. Kiji, T. Okano, A. Ooue, J. Mol. Catal. A-Chem. 1999, 147, 3–10;
13e
J. W. Raggon, W. M. Snyder, Org. Process Res. Dev. 2002, 6, 67–69.
14
14a
J. Dupont, C. S. Consorti, J. Spencer, Chem. Rev. 2005, 105, 2527–2571;
14b
S. B. Atla, A. A. Kelkar, V. G. Puranik, W. Bensch, R. V. Chaudhari, J. Organomet. Chem. 2009, 694, 683–690.
15
15a
T. Jeffery, B. Ferber, Tetrahedron Lett. 2003, 44, 193–197;
15b
K. Ferré-Filmon, L. Delaude, A. Demonceau, A. F. Noels, Coord. Chem. Rev. 2004, 248, 2323–2336;
15c
Á. Gordillo, E. de Jesús, C. López-Mardomingo, Chem. Commun. 2007, 4056–4058;
15d
M. Oberholzer, R. Gerber, C. M. Frecha, Adv. Synth. Catal. 2012, 354, 627–641;
Direct Link:
15e
L. Joucla, G. Cusati, C. Pinel, L. Djakovitcha, Adv. Synth. Catal. 2010, 352, 1993–2001.
Direct Link:
16
16a
B. Breit, Top. Curr. Chem. 2007, 279, 139–172;
16b
A. Gual, C. Godard, S. Castillón, C. Claver, Tetrahedron: Asymmetry 2010, 21, 1135–1146.
17
17a
M. Solinas, S. Gladiali, M. Marchetti, J. Mol. Catal. 2005, 226, 141–147;
17b
T. E. Lightburn, O. A. de Paolis, K. H. Cheng, K. L. Tan, Org. Lett. 2011, 13, 2686–2689.
18
M. Beller, B. Cornils, C. D. Frohning, C. W. Kohlpaintner, J. Mol. Catal. 1995, 104, 17–85.
19
19a
K. Takahashi, M. Yamashita, T. Ichihara, K. Nakano, K. Nozaki, Angew. Chem. 2010, 122, 4590–4592;
Direct Link:
Angew. Chem. Int. Ed. 2010, 49, 4488–4490;
Direct Link:
19b
T. Ichihara, K. Nakano, M. Katayama, K. Nozaki, Chem. Asian J. 2008, 3, 1722–1728.
Direct Link:
20
20a
M. O’Brien, P. Koos, D. L. Browne, S. V. Ley, Org. Biomol. Chem. 2012, 10, 7031–7036;
20b
D. X. Hu, U. Gross, M. O’Brien, P. Koos, D. L. Browne, S. V. Ley, Org. Lett. 2012, 14, 4246–4249.
21
21a
D. S. Surry, S. L. Buchwald, Chem. Sci. 2011, 2, 27–50;
21b
C. C. Mauger, G. A. Mignani, Aldrichimica Acta 2006, 39, 17–24;
- CAS,
- Web of Science® Times Cited: 42
21c
B. Schlummer, U. Scholz, Adv. Synth. Catal. 2004, 346, 1599–1626;
Direct Link:
21d
K. Billingsley, S. L. Buchwald, J. Am. Chem. Soc. 2007, 129, 3358–3366.
22
22a
T. Jeffery, Tetrahedron 1996, 52, 10113–10130;
22b
T. Jeffery in Advances in Metal-Organic Chemistry, Vol. 5 (Eds: L. S. Liebeskind), JAI Press Inc, 1996, pp. 153–260;
- Web of Science® Times Cited: 2
22c
M. T. Reetz, J. G. de Vries, Chem. Commun. 2004, 1559–1563;
22d
T. Jeffery, M. David, Tetrahedron Lett. 1998, 39, 5751–5754.
23
K. Ohrai, K. Kondo, M. Sodeoka, M. Shibasaki, J. Am. Chem. Soc. 1994, 116, 11737–11748.
24
24a
A. Beeby, S. Bettington, I. J. S. Fairlamb, A. E. Goeta, A. R. Kapdi, E. H. Niemela, A. L. Thompson, New J. Chem. 2004, 28, 600–605;
24b
I. J. S. Fairlamb, Chem. Soc. Rev. 2007, 36, 1036–1045;
24c
C. Sicre, A. A. C. Braga, F. Maseras, M. M. Cid, Tetrahedron 2008, 64, 7437–7443.
25
25a
A. F. Littke, G. C. Fu, J. Am. Chem. Soc. 2001, 123, 6989–7000;
25b
I. D. Hills, G. C. Fu, J. Am. Chem. Soc. 2004, 126, 13178–13179.
26
26a
C. F. Carter, I. R. Baxendale, M. O’Brien, J. B. J. Pavey, S. V. Ley, Org. Biomol. Chem. 2009, 7, 4594–4597;
26b
C. F. Carter, H. Lange, S. V. Ley, I. R. Baxendale, B. Wittkamp, J. G. Goode, N. L. Gaunt, Org. Process Res. Dev. 2010, 14, 393–404.
27
27a
K.-D. Wiese, D. Obst, Top. Organomet. Chem. 2006, 18, 1–33;
27b
A. van Rooy, E. N. Orij, P. C. J. Kamer, P. W. N. M. van Leeuwen, Organometallics 1995, 14, 34–43.
28
28a
A. Polo, C. Claver, S. Castillón, A. Rulz, Organometallics 1992, 11, 3525–3533;
28b
H. J. V. Barros, J. G. da Silva, C. C. Guimarães, E. N. dos Santos, E. V. Gusevskaya, Organometallics 2008, 27, 4523–4531.
29
29a
N. Sudheesh, S. K. Sharma, R. S. Shukla, R. V. Jasra, J. Mol. Catal. 2010, 316, 23–29;
29b
R. Lazzaroni, P. Pertici, S. Bertozzi, G. Fabrizi, J. Mol. Catal. 1990, 58, 75–85;
29c
J. P. Arhancet, M. E. Davis, B. E. Hanson, J. Catal. 1991, 129, 100–105;
29d
R. Lazzaroni, A. Raffaelli, R. Settambolo, S. Bertozzi, G. Vitulli, J. Mol. Catal. 1989, 50, 1–9.
30
30a
L. Yan, Y. Ding, J. Liu, H. Zhu, L. Lin, Chin. J. Catal. 2011, 32, 31–35;
30b
M. Diéguez, M. M. Pereira, A. Masdeu-Bultó, C. Claver, J. C. Bayón, J. Mol. Catal. 1999, 143, 111–122.
- CrossRef,
- Web of Science® Times Cited: 36
31
A. L. Watkins, C. R. Landis, J. Am. Chem. Soc. 2010, 132, 10306–10317.
32
T. Hayashi, M. Tanaka, I. Ogata, J. Mol. Catal. 1981, 13, 323–330.

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