Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2017; 49(05): 1024-1036
DOI: 10.1055/s-0036-1588894
DOI: 10.1055/s-0036-1588894
paper
Palladium-Catalyzed Direct α-Arylation of p-Methoxybenzyl-Protected S,S-Dimethylsulfoximine
Authors
Further Information
Publication History
Received: 28 July 2016
Accepted after revision: 12 September 2016
Publication Date:
12 October 2016 (online)
Abstract
Sulfoximines have recently gained considerable recognition as an important structural motif in the life sciences. This is especially true for (hetero)aryl-substituted S,S-dimethylsulfoximine derivatives, such as the marketed insecticide sulfoxaflor, as well as the clinical candidates PTEFb inhibitor BAY 1143572 and ATR inhibitor AZD 6738 for the treatment of cancer. Herein, the first palladium-catalyzed direct α-arylation of p-methoxybenzyl-protected S,S-dimethylsulfoximine using readily available (hetero)aryl bromides is reported. This new method provides a safe, short, and efficient approach to (hetero)aryl-substituted S,S-dimethylsulfoximine derivatives, an important class of bioactive compounds, demonstrated by application of this methodology to an improved synthesis of PTEFb inhibitor BAY 1143572.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588894.
- Supporting Information (PDF)
Primary Data
- Primary data for this article are available online at http://www.thieme-connect.com/products/ejournals/journal/10.1055/s-00000084
and can be cited using the following DOI: 10.4125/pd0084th.
- Primary Data (ZIP)
-
References
- 1 Bentley HR, McDermott EE, Pace J, Whitehead JK, Moran T. Nature 1949; 163: 675
- 3a Johnson CR. Acc. Chem. Res. 1973; 6: 341
- 3b Craig D, Grellepois F, White AJ. P. J. Org. Chem. 2005; 70: 6827
- 3c Gais H.-J, Babu GS, Günter M, Das P. Eur. J. Org. Chem. 2004; 1464
- 3d Harmata M, Hong X. J. Am. Chem. Soc. 2003; 125: 5754
- 3e Harmata M, Hong X, Barnes CL. Tetrahedron Lett. 2003; 44: 7261
- 3f Harmata M, Pavri N. Angew. Chem. Int. Ed. 1999; 38: 2419
- 3g Koep S, Gais H.-J, Raabe G. J. Am. Chem. Soc. 2003; 125: 13243
- 3h Shen X, Miao W, Ni C, Hu J. Angew. Chem. Int. Ed. 2014; 53: 775
- 3i Shen X, Liu Q, Zhang W, Hu J. Eur. J. Org. Chem. 2016; 906
- 4a Bolm C, Simic O. J. Am. Chem. Soc. 2001; 123: 3830
- 4b Harmata M, Ghosh SK. Org. Lett. 2001; 3: 3321
- 4c Bolm C, Martin M, Simic O, Verrucci M. Org. Lett. 2003; 5: 427
- 4d Bolm C, Felder M, Müller J. Synlett 1992; 439
- 4e Bolm C, Verrucci M, Simic O, Cozzi PG, Raabe G, Okamura H. Chem. Commun. 2003; 2826
- 4f Langner M, Bolm C. Angew. Chem. Int. Ed. 2004; 43: 5984
- 4g Langner M, Remy P, Bolm C. Chem. Eur. J. 2005; 11: 6254
- 4h Reetz MT, Bondarev OG, Gais H.-J, Bolm C. Tetrahedron Lett. 2005; 46: 5643
- 5 Lücking U. Angew. Chem. Int. Ed. 2013; 52: 9399
- 6a Satzinger G, Stoss P. Arzneim.-Forsch. 1970; 20: 1214
- 6b Dillard RD, Yen TT, Stark P, Parvey DE. J. Med. Chem. 1980; 23: 717
- 6c Ikeuchi H, Ahn Y.-M, Otokawa T, Watanabe B, Hegazy L, Hiratake J, Richards NG. J. Bioorg. Med. Chem. 2012; 20: 5915
- 7a Okamura H, Bolm C. Org. Lett. 2004; 6: 1305
- 7b Cho Y, Bolm C. Tetrahedron Lett. 2005; 46: 8007
- 7c García Mancheño O, Bolm C. Org. Lett. 2007; 9: 2951
- 7d Pandey A, Bolm C. Synthesis 2010; 2922
- 7e Gries J, Krüger J. Synlett 2014; 25: 1831
- 7f Lebel H, Piras H, Bartholomeüs J. Angew. Chem. Int. Ed. 2014; 53: 7300
- 7g Miao J, Richards NG. J, Ge H. Chem. Commun. 2014; 50: 9687
- 7h Dannenberg CA, Bizet V, Bolm C. Synthesis 2015; 47: 1951
- 7i Bizet V, Hendriks CM. M, Bolm C. Chem. Soc. Rev. 2015; 44: 3378
- 7j Zenzola M, Doran R, Luisi R, Bull JA. J. Org. Chem. 2015; 80: 6391
- 7k Zenzola M, Doran R, Degennaro L, Luisi R, Bull JA. Angew. Chem. Int. Ed. 2016; 55: 7203
- 8a Gutmann B, Elsner P, O’Kearney-McMullan A, Goundry W, Roberge DM, Kappe CO. Org. Process Res. Dev. 2015; 19: 1062
- 8b Lebel H, Piras H, Borduy M. ACS Catal. 2016; 6: 1109
- 9 Bizet V, Buglioni L, Bolm C. Angew. Chem. Int. Ed. 2014; 53: 5639
- 10a Zhu Y, Loso MR, Watson GB, Sparks TC, Rogers RB, Huang JX, Gerwick BC, Babcock JM, Kelley D, Hedge VB, Nugent BM, Renga JM, Denholm I, Gorman K, DeBoer GJ, Hasler J, Meade T, Thomas JD. J. Agric. Food Chem. 2011; 59: 2950
- 10b Lücking U, Jautelat R, Krüger M, Brumby T, Lienau P, Schäfer M, Briem H, Schulze J, Hillisch A, Reichel A, Wengner AM, Siemeister G. ChemMedChem 2013; 8: 1067
- 10c Goldberg FW, Kettle JG, Xiong J, Lin D. Tetrahedron 2014; 70: 6613
- 10d Goldberg FW, Kettle JG, Kogej T, Perry MW. D, Tomkinson NP. Drug Discovery Today 2015; 20: 11
- 10e Nishimura N, Norman MH, Liu L, Yang KC, Ashton KS, Bartberger MD, Chmait S, Chen J, Cupples R, Fotsch C, Helmering J, Jordan SR, Kunz RK, Pennington LD, Poon SF, Siegmund A, Sivits G, Lloyd DJ, Hale C, St Jean DJ. Jr. J. Med. Chem. 2014; 57: 3094
- 10f Boral S, Wang S, Malon T, Wurster J, Shen J, Robinson M (Allergan, Inc.) US Patent 20150166521, 2015 ; Chem. Abstr. 2015, 163, 118575.
- 10g Blum A (Boehringer Ingelheim) Patent WO 2015169677, 2015 ; Chem. Abstr. 2015, 163, 702466.
- 10h Johnson T, Vairagoundar R, Ewin RA (Zoetis LLC) Patent WO 2014172443, 2014 ; Chem. Abstr. 2014, 161, 647008.
- 10i Nugent BM, Buysse AM, Loso MR, Babcock JM, Johnson TC, Oliver MP, Martin TP, Ober MS, Breaux N, Robinson A, Adelfinskaya Y. Pest Manage. Sci. 2015; 71: 928
- 10j von Nussbaum F, Li VM.-J, Allerheiligen S, Anlauf S, Bärfacker L, Bechem M, Delbeck M, Fitzgerald MF, Gerisch M, Gielen-Haertwig H, Haning H, Karthaus D, Lang D, Lustig K, Meibom D, Mittendorf J, Rosentreter U, Schäfer M, Schäfer S, Schamberger J, Telan LA, Tersteegen A. ChemMedChem 2015; 10: 1163
- 10k See also ref. 5, and references cited therein.
- 11a Sparks TC, Watson GB, Loso MR, Geng C, Babcock JM, Thomas JD. Pestic. Biochem. Physiol. 2013; 107: 1
- 11b Arndt KE, Bland DC, Irvine NM, Powers SL, Martin TP, McConnell JR, Podhorez DE, Renga JM, Ross R, Roth GA, Scherzer BD, Toyzan TW. Org. Process Res. Dev. 2015; 19: 454
- 12 Luecking U, Scholz A, Lienau P, Siemeister G, Kosemund D, Bohlmann R, Eis K, Gnoth M, Terebesi I, Meyer K, Prelle K, Valencia R, Ince S, von Nussbaum F, Mumberg D, Ziegelbauer K, Klebl B, Choidas A, Nussbaumer P, Baumann M, Schultz-Fademrecht C, Ruehter G, Eickhoff J, Brands M. Cancer Res. 2015; 75 (15 Suppl): Abstract No. 2828
- 13 Foote KM, Lau A, Nissink JW. M. Future Med. Chem. 2015; 7: 873
- 14a Lücking U, Krueger M, Jautelat R, Siemeister G (Schering AG) Patent WO 2005037800, 2005 ; Chem. Abstr. 2005, 142, 430288.
- 14b Lücking U, Siemeister G, Jautelat R (Schering AG) Patent WO 2006099974, 2006 ; Chem. Abstr. 2006, 145, 377362.
- 14c Lücking U (Schering AG) Patent EP 1710246, 2006 ; Chem. Abstr. 2006, 145, 438651.
- 14d Lücking U, Kettschau G, Briem H, Schwede W, Schäfer M, Thierauch K.-H, Husemann M (Schering AG) Patent WO 2006108695, 2006 ; Chem. Abstr. 2006, 145, 419188.
- 14e Luecking U, Nguyen D, von Bonin A, von Ahsen O, Krueger M, Briem H, Kettschau G, Prien O, Mengel A, Krolikiewicz K, Boemer U, Bothe U, Hartung I (Schering AG) Patent WO 2007071455, 2007 ; Chem. Abstr. 2007, 147, 95692.
- 14f Lücking U, Siemeister G, Bader B (Schering AG) Patent WO 2007079982, 2007 ; Chem. Abstr. 2007, 147, 166339.
- 14g Luecking U, Siemeister G, Jautelat R (Bayer Schering Pharma AG) Patent WO 2008025556, 2008 ; Chem. Abstr. 2008, 148, 331698.
- 14h Prien O, Eis K, Lücking U, Guenther J, Zopf D (Bayer Schering Pharma AG) Patent DE 102007024470, 2008 ; Chem. Abstr. 2008, 150, 5753.
- 14i Hartung I, Bothe U, Kettschau G, Luecking U, Mengel A, Krueger M, Thierauch K.-H, Lienau P, Boemer U (Bayer Schering Pharma AG) Patent WO 2008155140, 2008 ; Chem. Abstr. 2009, 150, 214413.
- 14j Nguyen D, Von Bonin A, Haerter M, Schirok H, Mengel A, Von Ahsen O (Bayer Schering Pharma AG) Patent WO 2009089851, 2009 ; Chem. Abstr. 2009, 151, 173484.
- 14k Härter M, Beck H, Ellinghaus P, Berhoerster K, Greschat S, Thierauch K.-H, Süssmeier F (Bayer Schering Pharma AG) Patent WO 2010054763, 2010 ; Chem. Abstr. 2010, 152, 568149.
- 14l von Nussbaum F, Karthaus D, Anlauf S, Delbeck M, Li VM.-J, Meibom D, Lustig K, Schneider D (Bayer Schering Pharma AG) Patent WO 2010115548, 2010 ; Chem. Abstr. 2010, 153, 505832.
- 14m Schwede W, Klar U, Möller C, Rotgeri A, Bone W (Bayer Schering Pharma AG) Patent WO 2011009531, 2011 ; Chem. Abstr. 2011, 154, 158660.
- 14n Lücking U, Cleve A, Haendler B, Faus H, Köhr S, Irlbacher H (Bayer Schering Pharma AG) Patent WO 2011029537, 2011 ; Chem. Abstr. 2011, 154, 361030.
- 15 Lücking U, Bohlmann R, Scholz A, Siemeister G, Gnoth MJ, Boemer U, Kosemund D, Lienau P, Ruether G, Schulz-Fademrecht C (Bayer Intellectual Property GmbH) Patent WO 2012160034, 2012 ; Chem. Abstr. 2012, 158, 37597.
- 16a For an early example of an intramolecular coupling reaction, see: Bolm C, Okamura H, Verrucci M. J. Organomet. Chem. 2003; 687: 444
- 16b For an intermolecular coupling reaction, see: Cho GY, Bolm C. Org. Lett. 2005; 7: 1351
- 17 Zhou G, Ting PC, Aslanian RG. Tetrahedron Lett. 2010; 51: 939
- 18 Zheng B, Jia T, Walsh PJ. Org. Lett. 2013; 15: 1690
- 19 Nambo M, Crudden CM. Angew. Chem. Int. Ed. 2014; 53: 601
- 20a Bolm C, Hildebrand JP. Tetrahedron Lett. 1998; 39: 5731
- 20b Aithagani SK, Dara S, Munagala G, Aruri H, Yadav M, Sharma S, Vishwakarma RA, Pal Singh P. Org. Lett. 2015; 17: 5547 ; and references cited therein
- 21a Bordwell FG. Acc. Chem. Res. 1988; 21: 456
- 21b http://www.chem.wisc.edu/areas/reich/pkatable/ (accessed 9.9.2016).
- 22a See, for example, for Ts: Johnson CR, Lavergne O. J. Org. Chem. 1989; 54: 986
- 22b For Bz: Ref. 16b.
- 22c For TBDPS: Pandey AG, McGrath MJ, García Mancheño O, Bolm C. Synthesis 2011; 3827
- 23 For the cleavage of a PMB group via an intramolecular redox C–H activation process, see: Gao X, Gaddam V, Altenhofer E, Tata RR, Cai Z, Yongpruksa N, Garimallaprabhakaran AK, Harmata M. Angew. Chem. Int. Ed. 2012; 51: 7016
- 24a Since only formed in low amounts, potential diarylation products were not isolated and fully characterized; the corresponding mass ion was detected in various intensities upon monitoring the coupling reactions by UPLC/MS.
- 24b For the diarylation of methyl sulfones, see ref. 17.
- 25 Bruno N. Cross-Coupling Reaction Manual: Desk Reference. http://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Aldrich/Method/1/83784-Cross-Coupling-Selection-Brochure.pdf (accessed 9.9.2016)
- 26 See, for example: Morita DK, Stille JK, Norton JR. J. Am. Chem. Soc. 1995; 117: 8576
- 27 The racemate can be separated into the single enantiomers via chiral HPLC separation; see ref. 15.
- 28 Yadav MR, Rit RK, Sahoo AK. Chem. Eur. J. 2012; 18: 5541
- 29 García Mancheño O, Bistri O, Bolm C. Org. Lett. 2007; 9: 3809
See, for example:
See, for example:
See, for example: