Gold-Catalyzed Partial Hydrogenation of Activated Alkynes Mediated by Triphenylphosphine

Ana Patricia Cocoletzi-Xochitiotzi; Miguel Hernández-Hernández; Ignacio Medina-Mercado; Williams de Jesús Jiménez-Martínez; Virginia Maricela Mastranzo; Susana Porcel

doi:10.1055/s-0040-1707395

Synthesis, Table of Contents

Synthesis 2020; 52(16): 2379-2386
DOI: 10.1055/s-0040-1707395

paper

Gold-Catalyzed Partial Hydrogenation of Activated Alkynes Mediated by Triphenylphosphine

Ana Patricia Cocoletzi-Xochitiotzi

^aInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterios s/n, Ciudad Universitaria, Ciudad de México 04510, México Email: sporcel@unam.mx

^bUniversidad Autónoma de Tlaxcala, Facultad de Ciencias Básicas, Ingeniería y Tecnología, Calzada Apizaquito S/N 90300, Apizaco, Tlaxclala, México

,

Miguel Hernández-Hernández

^aInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterios s/n, Ciudad Universitaria, Ciudad de México 04510, México Email: sporcel@unam.mx

^bUniversidad Autónoma de Tlaxcala, Facultad de Ciencias Básicas, Ingeniería y Tecnología, Calzada Apizaquito S/N 90300, Apizaco, Tlaxclala, México

,

Ignacio Medina-Mercado

^aInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterios s/n, Ciudad Universitaria, Ciudad de México 04510, México Email: sporcel@unam.mx

,

Williams de Jesús Jiménez-Martínez

^aInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterios s/n, Ciudad Universitaria, Ciudad de México 04510, México Email: sporcel@unam.mx

,

Virginia Maricela Mastranzo

^aInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterios s/n, Ciudad Universitaria, Ciudad de México 04510, México Email: sporcel@unam.mx

^bUniversidad Autónoma de Tlaxcala, Facultad de Ciencias Básicas, Ingeniería y Tecnología, Calzada Apizaquito S/N 90300, Apizaco, Tlaxclala, México

,

Susana Porcel ∗

^aInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterios s/n, Ciudad Universitaria, Ciudad de México 04510, México Email: sporcel@unam.mx

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Abstract

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Abstract

Gold(I) can exhibit a cooperative effect with triphenylphosphine, accelerating the triphenylphosphine-mediated partial hydrogenation of activated alkynes. In this protocol, 3-arylpropiolates are selectively reduced to the Z-isomer when the aryl ring bears an electron-donor substituent, whereas 3-arylpropynones are reduced to the E-isomers.

Key words

partial hydrogenation - alkynes - triphenylphosphine - gold - catalysis

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References

References

For reviews on the Mitsunobu, Wittig, and Appel reactions, see:

1a Maryanoff BE, Reitz AB. Chem. Rev. 1989; 89: 863
1b Swamy KC. K, Kumar NN. B, Balaraman E, Kumar K. Chem. Rev. 2009; 109: 2551
1c de Andrade VS. C, de Mattos MC. S. Curr. Org. Chem. 2015; 12: 309

For recent reviews on phosphine-mediated organic reactions, see:

1d Xu S, He Z. RSC Adv. 2013; 3: 16885
1e Voituriez A, Saleh N. Tetrahedron Lett. 2016; 57: 4443
1f Zhou R, He Z. Eur. J. Org. Chem. 2016; 11: 1937
1g Guo H, Fan YC, Sun Z, Wu Y, Kwon O. Chem. Rev. 2018; 118: 10049
1h Nallapati SB, Chuang S.-C. Asian J. Org. Chem. 2018; 7: 1743

2 Richards EM, Tebby JC, Ward RS, Williams DH. J. Chem. Soc. C 1969; 1542

3a Larpent C, Meignan G. Tetrahedron Lett. 1993; 34: 4331
3b Tsai M.-S, Rao UN, Wang J.-R, Liang C.-H, Yeh M.-CP. J. Chin. Chem. Soc. 2001; 48: 869
3c Arbuzova SN, Glotova TE, Dvorko MY, Ushakov IA, Gusarova NK, Trofimov BA. ARKIVOC 2011; (xi): 183

4 Pierce BM, Simpon BF, Ferguson KH, Whittaker RE. Org. Biomol. Chem. 2018; 16: 6659

5a Blaser H.-U, Schnyder A, Steiner H, Rössler F, Baumeister P. In Handbook of Heterogeneous Catalysis . Wiley-VCH; Weinheim: 2008: 3284-3308
5b Heller D, De Vries AH, Vries JG. In Handbook of Homogeneous Hydrogenation, Vol. 3. de Vries JG, Elsevier CJ. Wiley-VCH; Weinheim: 2007: 1483-1516
5c Molnár A, Sàrkány A, Varga M. J. Mol. Catal. A: Chem. 2001; 173: 185

Selected examples:

6a Lindlar H. Helv. Chim. Acta 1952; 35: 446
6b Schrock RR, Osborn JA. J. Am. Chem. Soc. 1976; 98: 2143
6c Yoshida H, Kato M, Ogata T. J. Org. Chem. 1985; 50: 1147
6d Lindlar H, Dubuis R. Org. Synth. 2003; 46: 89
6e Gianetti TL, Tomson NC, Arnold J, Bergman RG. J. Am. Chem. Soc. 2011; 133: 14904
6f Lee Y, Motoyama Y, Tsuji K, Yoon S.-H, Mochida I, Nagashima H. ChemCatChem 2012; 4: 778
6g Mitsudome T, Yamamoto M, Maeno Z, Mizugaki T, Jitsukawa K, Kaneda K. J. Am. Chem. Soc. 2015; 137: 13452

For a review, see:

6h Oger C, Balas L, Durand T, Galano J.-M. Chem. Rev. 2013; 113: 1313

Selected examples:

7a Belger C, Neisius NM, Plietker B. Chem. Eur. J. 2010; 16: 12214
7b Li J, Hua R, Liu T. J. Org. Chem. 2010; 75: 2966
7c Semba K, Fujihara T, Xu T, Terao J. Adv. Synth. Catal. 2012; 354: 1542
7d Whittaker AM, Lalic G. Org. Lett. 2013; 15: 1112
7e Vasilikogiannaki E, Titilas I, Vassilikogiannakis G, Stratakis M. Chem. Commun. 2015; 51: 2384
7f 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; 52: 1800
7g Szeto KC, Sahyoun W, Merle N, Castelbou JL, Popoff N, Lefebvre F, Raynaud J, Godard C, Claver C, Delevoye L, Gauvin RM, Taoufik M. Catal. Sci. Technol. 2016; 6: 882
7h Li S.-S, Tao L, Wang F.-Z.-R, Liu Y.-M, Cao Y. Adv. Synth. Catal. 2016; 358: 1410
7i Korytiaková E, Thiel NO, Pape F, Teichert JF. Chem. Commun. 2017; 53: 732
7j Lam J, Szkop KM, Mosaferi E, Stephan DW. Chem. Soc. Rev. 2019; 48: 3592

8 Pasto DJ. In Comprehensive Organic Synthesis, Vol. 8. Trost BM, Fleming I. Pergamon; Oxford: 1991: 471

Selected examples:

9a Tani K, Iseki A, Yamagata T. Chem. Commun. 1999; 1821
9b Trost BM, Ball ZT, Jöge T. J. Am. Chem. Soc. 2002; 124: 7922
9c Trost BM, Ball ZT, Laemmerhold KM. J. Am. Chem. Soc. 2005; 127: 10028
9d Trost BM, Ball ZT. J. Am. Chem. Soc. 2005; 127: 17644
9e Reyes-Sánchez A, Cañavera-Buelvas F, Barrios-Francisco R, Cifuentes-Vaca OL, Flores-Alamo M, García JJ. Organometallics 2011; 30: 3340
9f Radkowshi K, Sundararaju B, Fürstner A. Angew. Chem. Int. Ed. 2013; 52: 355
9g Srimani D, Diskin-Posner Y, Ben-David Y, Milstein D. Angew. Chem. Int. Ed. 2013; 52: 14131
9h Leutzsch M, Wolf LM, Gupta P, Fuchs M, Thiel W, Farés C, Fürstner A. Angew.Chem. Int. Ed. 2015; 54: 12431
9i Rummelt SM, Radkowski K, Rosca D.-A, Fürstner A. J. Am. Chem. Soc. 2015; 137: 5506
9j Furukawa S, Komatsu T. ACS Catal. 2016; 6: 2121

For recent reviews see:

9k Michaelides IN, Dixon DJ. Angew. Chem. Int. Ed. 2013; 52: 806
9l Frihed TG, Fürstner A. Bull. Chem. Soc. Jpn. 2016; 89: 135
9m Swamy KC. K, Reddy AS, Sandeep K, Kalyani A. Tetrahedron Lett. 2018; 59: 419

Recent reviews on cooperative catalysis:

10a Afewerki S, Córdova A. Chem. Rev. 2016; 116: 13512
10b Wang MH, Sheidt KA. Angew. Chem. Int. Ed. 2016; 55: 14912
10c Kathe P, Fleischer I. ChemCatChem 2019; 11: 3343
10d Gupta GR, Shah J, Vadagaonkar KS, Lavekar AG, Kapdi AR. Org. Biomol. Chem. 2019; 17: 7596

Recent reviews:

11a Hashmi AS. K. Angew. Chem. Int. Ed. 2010; 49: 5232
11b Alcaide B, Almendros P, Alonso JM. Molecules 2011; 16: 7815
11c Alcaide B, Almendros P, Alonso JM. Org. Biomol. Chem. 2011; 9: 4405
11d Hashmi AS. K. Acc. Chem. Res. 2014; 47: 864
11e Fürstner A. Acc. Chem. Res. 2014; 47: 925
11f Alcaide B, Almendros P. Acc. Chem. Res. 2014; 47: 939
11g Zhang Y, Luo T, Yang Z. Nat. Prod. Rep. 2014; 31: 489
11h Dorel R, Echavarren AM. Chem. Rev. 2015; 115: 9028
11i Goodwin JA, Aponick A. Chem. Commun. 2015; 51: 8730
11j Lo VK.-Y, Chan AO.-Y, Che C.-M. Org. Biomol. Chem. 2015; 13: 6667
11k Zi W, Toste FD. Chem. Soc. Rev. 2016; 45: 4567
11l Plästerer D, Hashmi AS. K. Chem. Soc. Rev. 2016; 45: 1331
11m Ahlsten N, Arcadi A, Cambeiro XC, Cao Z.-Y, Larrosa I, López F, Mascareñas JL, Miles DH, Muñoz MP, Perry GJ. P, Quirós MT, Toste FD, Wang Y.-H, Ye L, Zang L, Zhou J. Au-Catalyzed Synthesis and Functionalization of Heterocycles . In Topics in Heterocyclic Chemistry, Vol. 46. Bandini M. Springer; Switzerland: 2016
11n Fürstner A. Angew. Chem. Int. Ed. 2018; 57: 4215
11o Fang W, Shi M. Chem. Eur. J. 2018; 24: 9998
11p Mertens RT, Awuah SG. Gold Catalysis: Fundamentals and Recent Developments . In Catalysis by Metal Complexes Nanomaterials . Zhou M. ACS Symposium Series 1317; American Chemical Society; Washington DC: 2019. Chap. 2, 19-55

12 Savioa D, Tagliavini E, Trombini C, Umani-Ronchi A. J. Org. Chem. 1981; 46: 5340
13 Kim H.-J, Lindesey JS. J. Org. Chem. 2005; 70: 5475
14 Mueller A, Jennings MP. Org. Lett. 2007; 9: 5327
15 Shi Z, He C. J. Org. Chem. 2004; 69: 3669
16 Riccaboni M, La Porta E, Martorana A, Attanasio R. Tetrahedron 2010; 66: 4032
17 Kojima S, Takagi R, Akiba K.-Y. J. Am. Chem. Soc. 1997; 119: 5970

18a Lebel H, Davi M. Adv. Synth. Catal. 2008; 350: 2352
18b Cheng G, Mirafzal GA, Woo LK. Organometallics 2003; 22: 1468

19 Cheng G, Mirafzal GA, Woo LK. Organometallics 2003; 22: 1468
20 Chen Y, Huang L, Ranade MA, Zang XP. J. Org. Chem. 2003; 68: 3714
21 Moreno-Mañas M, Perez M, Pleixats R. Tetrahedron Lett. 1996; 41: 7449
22 Walter C, Oestreich M. Angew. Chem. Int. Ed. 2008; 47: 3818
23 Beveridge RE, Arndtsen BA. Synthesis 2010; 1000
24 Schmink JR, Holcomb JL, Leadbeater NE. Org. Lett. 2009; 11: 365
25 Romanelli G, Pasquale G, Sathicq A, Thomas H, Autino J, Vázquez P. J. Mol. Catal. A: Chem. 2011; 340: 24
26 Fiorilli S, Onida B, Barolo C, Viscardi G, Brunel D, Garrone E. Langmuir 2007; 23: 2261
27 Solin N, Han L, Che S, Terasaki O. Catal. Commun. 2009; 10: 1386

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