Lanthanoids in Hydroarylaminations: Yb(III)- and Tb(III)-Catalyzed Addition of Arylamines to Activated Olefins

Dedicated to the Late Prof. Ibrahim Ibnusaud, Founder Director, IIRBS, M. G. University, Kottayam, Kerala

Abstract

Michael-type hydroaminations of acrylonitrile, phenyl vinyl sulfone, and dimethyl maleate were realized using arylamines catalyzed independently by Yb(OTf)₃ and Tb(OTf)₃ to give the desired β-aminonitriles, β-amino sulfones, and dimethyl aspartates, respectively, in moderate to excellent yields. The reactions were carried out in toluene for Yb(OTf)₃ and in t-BuOMe for Tb(OTf)₃, all reactions were performed at 100 °C.

Key words

aza-Michael addition - β-amino acid derivatives - β-amino sulfones - lanthanide triflates - catalyst - terbium(III) triflate - ytterbium(III) triflate

Publication History

Received: 16 December 2023

Accepted after revision: 06 March 2024

Accepted Manuscript online:
06 March 2024

Article published online:
25 March 2024

• References

• 1a Yaşa H, Demir K. J. Turk. Chem. Soc., Sect. A 2019; 6: 433
• 1b Filho JF. A, Lemos BC, de Souza AS, Pinheiro S, Greco SJ. Tetrahedron 2017; 73: 6977
• 1c Huang PJ. J, Youssef D, Cameron TS, Jha A. ARKIVOC 2008; (xvi): 165
• 1d Ji J.-X, Qiu L.-Q, Yip CW, Chan AS. C. J. Org. Chem. 2003; 68: 1589
• 2a Chen M, Sun W, Yang J, Yuan L, Chen JQ, Wu J. Green Chem. 2023; 25: 3857
• 2b Long J, Gao W, Guan Y, Lv H, Zhang X. Org. Lett. 2018; 20: 5914
• 2c Zhang H, Li Y, Xu W, Zheng W, Zhou P, Sun Z. Org. Biomol. Chem. 2011; 9: 6502
• 2d Velázquez F, Arasappan A, Chen K, Sannigrahi M, Venkatraman S, McPhail AT, Chan T.-M, Shih N.-Y, Njoroge FG. Org. Lett. 2006; 8: 789
• 2e McIntyre JA, Castaner J. Drugs Future 2004; 29: 985
• 2f Tamamura H, Koh Y, Ueda S, Sasaki Y, Yamasaki T, Aoki M, Maeda K, Watai Y, Arikuni H, Otaka A, Mitsuya H, Fujii N. J. Med. Chem. 2003; 46: 1764
• 2g Becker DP, Barta TE, Bedell L, De Crescenzo G, Freskos J, Getman DP, Hockerman SL, Li M, Mehta P, Mischke B, Munie GE, Swearingen C, Villamil CI. Bioorg. Med. Chem. Lett. 2001; 11: 2719
• 2h Enders D, Müller SF, Raabe G. Angew. Chem. Int. Ed. 1999; 38: 195
• 3a Saha S, Chatterjee A, Banerjee M. J. Org. Chem. 2023; 88: 15358
• 3b Nonn M, Drahos L, Kiss L. ChemistrySelect 2023; 8: e202303898
• 3c Rulev AY. Eur. J. Org. Chem. 2023; e202300451
• 3d Zhang Z, Wang J, Yu M, Ye S, Wu J. Org. Lett. 2022; 25: 304
• 3e Prabhakara MD, Maiti B. Res. Chem. Intermed. 2020; 46: 2381
• 3f Singh R, Bhasin G, Srivastava R. Mini-Rev. Org. Chem. 2016; 13: 143
• 3g Soloshonok VA, Sorochinsky AE. Synthesis 2010; 2319
• 3h Wang Q, Dau M.-ET. H, Sasaki NA, Potier P. Tetrahedron 2001; 57: 6455
• 3i Roche H, Cure H, Adenis A, Fargeot P, Terret C, Lentz MA, Madelmont JC, Fumoleau P, Hanauske A, Chollet P. J. Neuro-Oncol. 2000; 49: 141
• 3j Pauly R, Sasaki A, Portier P. Tetrahedron Lett. 1994; 35: 237
• 3k de Blas J, Carretero JC, Dominguez E. Tetrahedron Lett. 1994; 35: 4603
• 3l Carmine AA, Brogden RN, Heel RC, Speight TM, Avery GS. Drugs 1982; 24: 85
• 4a Li W, Zhang J. Chem. Soc. Rev. 2016; 45: 1657
• 4b Lyu A, Fang L, Gou S. Eur. J. Med. Chem. 2014; 87: 631
• 4c Carroll MP, Guiry PJ. Chem. Soc. Rev. 2014; 43: 819
• 4d Stepanova VA, Smoliakova IP. Curr. Org. Chem. 2012; 16: 2893
• 4e Rano TA, Kuo GH. Org. Lett. 2009; 11: 2812
• 4f Man HW, Schafer P, Wong LM, Patterson RT, Corral LG, Raymon H, Blease K, Leisten J, Shirley MA, Tang Y, Babusis DM, Chen R, Stirling D, Muller GW. J. Med. Chem. 2009; 52: 1522
• 4g Aranapakam V, Grosu GT, Davis JM, Hu B, Ellingboe J, Baker JL, Skotnicki JS, Zask A, DiJoseph JF, Sung A, Sharr MA, Killar LM, Walter T, Jin G, Cowling R. J. Med. Chem. 2003; 46: 2361
• 4h Wada CK, Holms JH, Curtin ML, Dai Y, Florjancic AS, Garland RB, Guo Y, Heyman HR, Stacey JR, Steinman DH, Albert DH, Bouska JJ, Elmore IN, Goodfellow CL, Marcotte PA, Tapang P, Morgan DW, Michaelides MR, Davidsen SK. J. Med. Chem. 2002; 45: 219
• 4i Becker DP, DeCrescenzo G, Freskos J, Getman DP, Hockerman SL, Li M, Mehta P, Munie GE, Swearingen C. Bioorg. Med. Chem. Lett. 2001; 11: 2723
• 4j Ager DJ, Prakash I, Schaad DR. Chem. Rev. 1996; 96: 835
• 5a Meskini I, Toupet L, Daoudi M, Kerbal A, Bennani B, Dixneuf PH, Chohan ZH, Leite AC. L, Hadda TB. J. Braz. Chem. Soc. 2010; 21: 1129
• 5b Bacchi A, Biemmi M, Carcelli M, Carta F, Compari C, Fisicaro E, Rogolino D, Sechi M, Sippel M, Sotriffer CA, Sanchez TW, Neamati N. J. Med. Chem. 2008; 51: 7253
• 5c Sechi M, Bacchi A, Carcelli M, Compari C, Duce E, Fisicaro E, Rogolino D, Gates P, Derudas M, Al-Mawsawi LQ, Neamati N. J. Med. Chem. 2006; 49: 4248
• 6a Li M, Xia H.-F, Yang L.-Y, Hong T, Xie LJ, Li S, Wu J. RSC Adv. 2019; 9: 9187
• 6b Cabrele C, Martinek TA, Reiser O, Berlicki Ł. J. Med. Chem. 2014; 57: 9718
• 6c Horne WS. Expert Opin. Drug Discovery 2011; 6: 1247
• 6d Goodman CM, Choi S, Shandler S, DeGrado WF. Nat. Chem. Biol. 2007; 3: 252
• 6e Koyack MJ, Cheng RP. Methods Mol. Biol. 2006; 340: 95
• 6f Fülöp F, Martinek TA, Toth GK. Chem. Soc. Rev. 2006; 35: 323
• 6g Seebach D, Beck AK, Bierbaum DJ. Chem. Biodiversity 2004; 1: 1111
• 6h Cheng RP, Gellman SH, DeGrado WF. Chem. Rev. 2001; 101: 3219
• 6i Gellman SH. Acc. Chem. Res. 1998; 31: 173
• 6j Myers JK, Jacobsen EN. J. Am. Chem. Soc. 1999; 121: 8959
• 6k Enantioselective Synthesis of β-Amino Acids, 2nd ed. Juaristi E, Soloshonok VA. Wiley-VCH; Weinheim: 1997
• 7a Yamuna P, Philip RM, Anilkumar G. Tetrahedron 2022; 122: 132936
• 7b Song YX, Du DM. Adv. Synth. Catal. 2021; 363: 4667
• 7c Sharma P, Gupta R, Bansal RK. Beilstein J. Org. Chem. 2021; 17: 2585
• 7d Malkar RS, Jadhav AL, Yadav GD. J. Mol. Catal. 2020; 485: 110814
• 7e Zheng K, Liu X, Feng X. Chem. Rev. 2018; 118: 7586
• 7f Sanchez-Rosello M, Acena JL, Simon-Fuentes A, Del Pozo C. Chem. Soc. Rev. 2014; 43: 7430
• 7g Zhang J, Zhang Y, Liu X, Guo J, Cao W, Lin L, Feng X. Adv. Synth. Catal. 2014; 356: 3545
• 7h Bosica G, Debono AJ. Tetrahedron 2014; 70: 6607
• 7i Reyes-Sánchez A, García-Ventura I, García JJ. Dalton Trans. 2014; 43: 1762
• 7j Amara Z, Caron J, Joseph D. Nat. Prod. Rep. 2013; 30: 1211
• 7k Wang J, Li P, Choy PY, Chan AS. C, Kwong FY. ChemCatChem 2012; 4: 917
• 7l Rulev AY. Russ. Chem. Rev. 2011; 80: 197
• 7m Wang J, Wang W, Liu X, Hou Z, Lin L, Feng X. Eur. J. Org. Chem. 2011; 2039
• 7n Jiang J, Cai Y, Chen W, Lin L, Liu X, Feng X. Chem. Commun. 2011; 47: 4016
• 7o Azizi N, Baghi R, Ghafuri H, Bolourtchian M, Hashemi M. Synlett 2010; 379
• 7p Krishna PR, Sreeshailam A, Srinivas R. Tetrahedron 2009; 65: 9657
• 7q Enders D, Wang C, Liebich JX. Chem. Eur. J. 2009; 15: 11058
• 7r Zou B, Jiang H.-F. Chin. J. Chem. 2008; 26: 1309
• 7s Taimur A, Ravinder RK. Chin. J. Chem. 2008; 26: 751
• 7t Vicario JL, Badía D, Carrillo L. Synthesis 2007; 2065
• 7u Yang L, Xu LW, Xia CG. Tetrahedron Lett. 2007; 48: 1599
• 7v Ranu BC, Banerjee S. Tetrahedron Lett. 2007; 48: 141
• 7w Yadav JS, Reddy AR, Rao YG, Narsaiah AV, Reddy BV. S. Synthesis 2007; 3447
• 7x Narsaiah AV. Lett. Org. Chem. 2007; 4: 462
• 7y Varala R, Sreelatha N, Adapa SR. Synlett 2006; 1549
• 7z Reddy KR, Kumar NS. Synlett 2006; 2246
• 7aa Xu L.-W, Xia C.-G. Eur. J. Org. Chem. 2005; 633
• 7ab Vicario JL, Badía D, Carrillo L, Etxebarria J, Reyes E, Ruiz N. Org. Prep. Proced. Int. 2005; 37: 513
• 7ac Chaudhuri M. K., Hussain S., Kantam M. L., Neelima B.; Tetrahedron Lett.; 2005, 46 8329
• 7ad Kantam ML, Neelima B, Reddy CV. J. Mol. Catal. A: Chem. 2005; 241: 147
• 7ae Xu L.-W, Li J.-W, Zhou S.-L, Xia C.-G. New J. Chem. 2004; 28: 183
• 7af Azizi N, Saidi MR. Tetrahedron 2004; 60: 383
• 7ag Varala R, Alam MM, Adapa SR. Synlett 2003; 720
• 7ah Yadav JS, Reddy BV. S, Basak AK, Narsaiah AV. Chem. Lett. 2003; 32: 988
• 7ai Shaikh SN, Deshpande HV, Bedekar AV. Tetrahedron 2001; 57: 9045
• 7aj Bartoli G, Bosco M, Marcantoni E, Petrini M, Sambri L, Torregiani EJ. J. Org. Chem. 2001; 66: 9052
• 7ak Kawatsura M, Hartwig JF. Organometallics 2001; 20: 1960
• 7al Moghaddam FM, Mohammadi M, Hosseinni A. Synth. Commun. 2000; 30: 643
• 7am Enders D, Muller SF, Raabe G, Runsink J. Eur. J. Org. Chem. 2000; 879
• 7an Loh TP, Wei LL. Synlett 1998; 975
• 7ao Jenner G. Tetrahedron Lett. 1995; 36: 233
• 7ap Matsubara S, Yoshioka M, Utimoto K. Chem. Lett. 1994; 23: 827
• 8a Tyagi A, Mondal S, Anmol, Tiwari V, Karmakar T, Kundu S. Chem. Commun. 2023; 59: 110
• 8b Duraisamy T, Govindan K, Seenivasan VT, Chen NQ, Liao ZX, Lin WY. Asian J. Org. Chem. 2023; 12: e202300367
• 8c Rajesh R, Garg JA, Thiruvengetam P, Kunjanpillai R. Asian J. Org. Chem. 2022; 11: e202200440
• 8d Fedotova A, Kondrashov E, Legros J, Maddaluno J, Rulev AY. C. R. Chim. 2018; 21: 639
• 8e Kour M, Paul S. Monatsh. Chem. 2017; 148: 327
• 8f Hosseinzadeh R, Aghili N, Tajbakhsh M. Catal. Lett. 2016; 146: 1194
• 8g Kim S, Kang S, Kim G, Lee Y. J. Org. Chem. 2016; 81: 4048
• 8h Lapointe S, Zargarian D. Dalton Trans. 2016; 45: 15800
• 8i Solè D, Pèrez-Janer F, Mancuso R. Chem. Eur. J. 2015; 21: 4580
• 8j Dewan M, De A, Mozumdar S. Inorg. Chem. Commun. 2015; 53: 92
• 8k Sakai N, Takahashi N, Ogiwara Y. Eur. J. Org. Chem. 2014; 5078
• 8l Stevanovic D, Pejović A, Damljanović I, Vukićević M, Bogdanović GA, Vukićević RD. Tetrahedron Lett. 2012; 53: 6257
• 8m Choudhary VR, Dumbre DK, Patil SK. RSC Adv. 2012; 2: 7061
• 8n Kilic H, Bayindir S, Erdogan E, Saracoglu N. Tetrahedron 2012; 68: 5619
• 8o Salah AB, Offenstein C, Zargarian D. Organometallics 2011; 30: 5352
• 8p Lefèvre X, Durieux G, Lesturgez S, Zargarian D. J. Mol. Catal. A: Chem. 2011; 335: 1
• 8q Rajabi F, Razavi S, Luque R. Green Chem. 2010; 12: 786
• 8r Roy A, Kundu D, Kundu SK, Majee A, Hajra A. Open Catal. J. 2010; 3: 34
• 8s Reboule I, Bezzenine-Lafollee S, Collin J, Gil R, Martin M. Lett. Org. Chem. 2010; 7: 94
• 8t Ai X, Wang X, Liu JM, Ge ZM, Cheng TM, Li RT. Tetrahedron 2010; 66: 5373
• 8u Liu XB, Lu M, Lu TT, Gu GL. J. Chin. Chem. Soc. 2010; 57: 1221
• 8v De K, Legros J, Crousse B, Bonnet-Delpon D. J. Org. Chem. 2009; 74: 6260
• 8w Ying AG, Wang LM, Deng HX, Chen JH, Chen XZ, Yeb WD. ARKIVOC 2009; (xi): 288
• 8x Saidi MR, Pourshojaei Y, Aryanasab F. Synth. Commun. 2009; 39: 1109
• 8y Castonguay A, Spasyuk DM, Madern N, Beauchamp AL, Zargarian D. Organometallics 2009; 28: 2134
• 8z Damera K, Reddy KL, Sharma GV. M. Lett. Org. Chem. 2009; 6: 151
• 8aa Bhanushali MJ, Nandurkar NS, Jagtap SR, Bhanage BM. Catal. Commun. 2008; 9: 1189
• 8ab Chen X, She J, Shang Z, Wu J, Zhang P. Synthesis 2008; 3931
• 8ac Munro-Leighton C, Delp SA, Blue ED, Gunnoe TB. Organometallics 2007; 26: 1483
• 8ad Kawatsura M, Aburatanib S, Uenishi J. Tetrahedron 2007; 63: 4172
• 8ae Kantam ML, Neelima B, Reddy CV, Rajashree C. Ind. Eng. Chem. Res. 2007; 46: 8614
• 8af Munro-Leighton C, Blue ED, Gunnoe TB. J. Am. Chem. Soc. 2006; 128: 1446
• 8ag Duan Z, Xuan X, Li T, Yang C, Wu Y. Tetrahedron Lett. 2006; 47: 5433
• 8ah Leitch S, Addison-Jones J, McCluskey A. Tetrahedron Lett. 2005; 46: 2915
• 8ai Reboule I, Gil R, Collin J. Tetrahedron Lett. 2005; 46: 7761
• 8aj Xu L.-W, Li L, Xia C.-G. Helv. Chim. Acta 2004; 87: 1522
• 8ak Xu LW, Xia CG. Synthesis 2004; 2191
• 8al Srivastava N, Banik BK. J. Org. Chem. 2003; 68: 2109
• 8am Wabnitz TC, Spencer JB. Tetrahedron Lett. 2002; 43: 3891
• 8an Cabral J, Laszlo P, Mahé L, Montaufier MT, Randriamahefa SL. Tetrahedron Lett. 1989; 30: 3969
• 9a Wu YH, Zhang LY, Wang NX, Xing Y. Catal. Rev. Sci. Eng. 2022; 64: 679
• 9b Pellissier H. Coord. Chem. Rev. 2017; 336: 96
• 9c Mikami K, Terada M, Matsuzawa H. Angew. Chem. Int. Ed. 2002; 41: 3554
• 9d Kobayashi S, Hamada T, Nagayama S, Manabe K. Org. Lett. 2001; 3: 165
• 10 Cotton S. The Lanthanides . In Lanthanides and Actinides . Macmillan PhysicalScience Series. Macmillan Education; Basingstoke: 1991: 10-84
• 11 Cotton SA. C. R. Chim. 2005; 8: 129
• 12 Miller M, Vogel JC, Tsang W, Merrit A, Procter DJ. Org. Biomol. Chem. 2009; 7: 589
• 13 Bashford KE, Cooper AL, Kane PD, Moody CJ, Muthusamy S, Swann E. J. Chem. Soc., Perkin Trans. 1 2002; 1672
• 14 King SM, Buchwald SL. Org. Lett. 2016; 18: 4128