On Gold-Mediated C-H
Activation Processes

Teresa de Haro; Cristina Nevado

doi:10.1055/s-0030-1260122

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

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2011(16): 2530-2539
DOI: 10.1055/s-0030-1260122

REVIEW

On Gold-Mediated C-H Activation Processes

Teresa de Haro, Cristina Nevado*
Organic Chemistry Institute, University of Zürich, Winterthurerstr. 190, 8057 Zürich, Switzerland
Fax: +41(44)6356812; e-Mail: nevado@oci.uzh.ch;

Further Information

Publication History

Received 20 May 2011
Publication Date:
14 July 2011 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

The ubiquitous nature of C-H bonds in organic molecules offers unparalleled opportunities for the development of more efficient methods to construct functionalized molecules. Recent advances in the developing area of gold-catalyzed C-H activation will be summarized here.

1 Introduction

2 Gold-Catalyzed Csp-H Activation Processes

2.1 Gold Acetylides as Nucleophiles

2.2 Gold Acetylides in Redox Processes

3 Gold-Catalyzed Csp^²-H Activation Processes

3.1 Csp^²-H Bond Activation by Gold(III)

3.2 Csp^²-H Bond Activation by Gold(I)

4 Gold-Catalyzed Csp^³-H Activation Processes

4.1 Csp^³-H Activation by Gold-Carbene-Induced C-H Insertion

5 Conclusions

Key words

gold - catalysis - homogeneous catalysis - metalation - C-H activation

References

1 Godula K. Sames D. Science 2006, 312: 67

Crossref PubMed Google Scholar
2a Labinger JA. Bercaw JE. Nature 2002, 417: 507

Google Scholar
2b Dyker G. Angew. Chem. Int. Ed. 1999, 38: 1698

Google Scholar
2c Shilov AE. Shul’pin GB. Chem. Rev. 1997, 97: 2879

Google Scholar
3a Ritleng V. Sirlin C. Pfeffer M. Chem. Rev. 2002, 102: 1731

Google Scholar
3b Kakiuchi F. Murai S. Acc. Chem. Res. 2002, 35: 826

Google Scholar
3c Murakami M. Ito Y. Top. Organomet. Chem. 1999, 3: 97

Google Scholar
4 Jones WD. Top. Organomet. Chem. 1999, 3: 9

Google Scholar
5a Jia C. Kitamura T. Fujiwara Y. Acc. Chem. Res. 2001, 34: 633

Google Scholar
5b Kakiuchi F. Murai S. Top. Organomet. Chem. 1999, 3: 47

Google Scholar
6a Boorman TC. Larrosa I. Chem. Soc. Rev. 2011, 40: 1910

Google Scholar
6b Skouta R. Li C.-J. Tetrahedron 2008, 64: 4917

Google Scholar
6c He C. Li Z. Brouwer C. Chem. Rev. 2008, 108: 3239

Google Scholar
7a Arndtsen BA. Bergman RG. Mobley TA. Peterson TH. Acc. Chem. Res. 1995, 28: 154

Google Scholar
7b Stahl SS. Labinger JA. Bercaw JE. Angew. Chem. Int. Ed. 1998, 37: 2180

Google Scholar
7c Díaz-Requejo MM. Pérez P. Chem. Rev. 2008, 108: 3379

Google Scholar
8 Fürstner A. Davies PW. Angew. Chem. Int. Ed. 2007, 46: 3410

Crossref PubMed Google Scholar
9a Cross RJ. Davidson MF. McLennan AJ. J. Organomet. Chem. 1984, 265: C37

Google Scholar
9b Chao H.-Y. Lu W. Li Y. Chan MCW. Che C.-M. Cheung K.-K. Zhu N. J. Am. Chem. Soc. 2002, 124: 14696

Google Scholar
9c Whittall IR. Humphrey MG. Houbrechts S. Persoons A. Hockless DCR. Organometallics 1996, 15: 5738

Google Scholar
10 Schuster O. Liau R.-Y. Schier A. Schmidbaur H. Inorg. Chim. Acta 2005, 358: 1429

Crossref Google Scholar
11 Fortman GC. Poater A. Levell JW. Gaillard S. Slawin AMZ. Samuel IDW. Cavallo L. Nolan SP. Dalton Trans. 2010, 39: 10382

Crossref Google Scholar
12 Wei C. Li C.-J. J. Am. Chem. Soc. 2003, 125: 9584

Crossref Google Scholar
13 Lo VK.-Y. Liu Y. Wong M.-K. Che C.-M. Org. Lett. 2006, 8: 1529

Crossref Google Scholar
14a Kantam ML. Prakash BV. Reddy CRV. Sreedhar B. Synlett 2005, 2329

Google Scholar
14b Kidwai M. Bansal V. Kumarb A. Mozumdar S. Green Chem. 2007, 9: 742

Google Scholar
15 Li C. Li W. Wang J. Tetrahedron Lett. 2009, 50: 2533

Crossref Google Scholar
16 Yan B. Liu Y. Org. Lett. 2007, 9: 4323

Crossref PubMed Google Scholar
17 Xiao F. Chen Y. Liu Y. Wang J. Tetrahedron 2008, 64: 2755

Crossref Google Scholar
18 Yao X. Li C.-J. Org. Lett. 2006, 8: 1953

Crossref PubMed Google Scholar
19 Li C. Mo F. Li W. Wang J. Tetrahedron Lett. 2009, 65: 6053

Google Scholar
20 Leyva-Pérez A. Rubio-Marqués P. Al-Deyab SS. Al-Resayes SI. Corma A. ACS Catal. 2011, 1: 601

Crossref Google Scholar
For a recent review on palladium-catalyzed alkynylation see:
21a Negishi E. Anastasia L. Chem. Rev. 2003, 103: 1979

Google Scholar
21b Chinchilla R. Nájera C. Chem. Rev. 2007, 107: 874

Google Scholar
22 Jones LA. Sanz S. Laguna M. Catal. Today 2007, 122: 403

Crossref Google Scholar
23 González-Arellano C. Abad A. Corma A. García H. Iglesias M. Sánchez F. Angew. Chem. Int. Ed. 2007, 46: 1536

Crossref Google Scholar
24 de Souza ROMA. Bittar MS. Mendes LVP. da Silva CMF. da Silva VT. Antunes OAC. Synlett 2008, 1777

Article in Thieme Connect Google Scholar
26 Li P. Wang L. Wang M. You F. Eur. J. Org. Chem. 2008, 5946

Google Scholar
27 Lauterbach T. Livendahl M. Roselln A. Espinet P. Echavarren AM. Org. Lett. 2010, 12: 3006

Crossref PubMed Google Scholar
28 Kyriakou G. Beaumont SK. Humphrey SM. Antonetti C. Lambert RM. ChemCatChem 2010, 2: 1444

Crossref Google Scholar
29 Corma A. Juárez R. Boronat M. Sánchez F. Iglesias M. García H. Chem. Commun. 2011, 47: 1446

Crossref PubMed Google Scholar
30 de Haro T. Nevado C. J. Am. Chem. Soc. 2010, 132: 1512

Crossref Google Scholar
31 Hopkinson MN. Ross JE. Giuffredi GT. Gee AD. Gouverneur V. Org. Lett. 2010, 12: 4904

Crossref PubMed Google Scholar
32a Kharasch MS. Isbell HS. J. Am. Chem. Soc. 1931, 53: 3053

Google Scholar
32b Kharasch MS. Beck TM. J. Am. Chem. Soc. 1934, 56: 2057

Google Scholar
33a Liddle KS. Parkin C. J. Chem. Soc., Chem. Commun. 1972, 26

Google Scholar
33b de Graaf PWJ. Boersma J. van der Kerk GJM. J. Organomet. Chem. 1976, 105: 399

Google Scholar
33c Zhu Y. Cameron BR. Skerlj RT. J. Organomet. Chem. 2003, 677: 57 ; and references therein

Google Scholar
34 Fuchita Y. Utsunomiya Y. Yasutake M. J. Chem. Soc., Dalton Trans. 2001, 2330

Google Scholar
35a Brand J. Charpentier J. Waser J. Angew. Chem. Int. Ed. 2009, 48: 9346

Google Scholar
35b Brand JP. Waser J. Angew. Chem. Int. Ed. 2010, 49: 7304

Google Scholar
37 Hashmi ASK. Schwarz L. Choi J.-H. Frost TM. Angew. Chem. Int. Ed. 2000, 39: 2285

Crossref PubMed Google Scholar
38a Aguilar D. Contel M. Navarro R. Urriolabeitia EP. Organometallics 2007, 26: 4604

Google Scholar
38b Aguilar D. Contel M. Navarro R. Soler T. Urriolabeitia EP. J. Organomet. Chem. 2009, 694: 486

Google Scholar
39 However, further studies demonstrated that this reaction also can be catalyzed under appropriate conditions by a Brønsted acid with a non-nucleophilic counterion: Dyker G. Muth E. Hashmi ASK. Ding L. Adv. Synth. Catal. 2003, 345: 1247

Crossref Google Scholar
40 Arcadi A. Bianchi G. Chiarini M. D’Anniballe G. Marinelli F. Synlett 2004, 944

Article in Thieme Connect Google Scholar
41 Alfonsi M. Arcadi A. Bianchi G. Marinelli F. Nardini A. Eur. J. Org. Chem. 2006, 2393

Google Scholar
42a Li Z. Shi Z. He C. J. Organomet. Chem. 2005, 690: 5049

Google Scholar
42b Xiao Y.-P. Liu X.-Y. Che C.-M. J. Organomet. Chem. 2009, 694: 494

Google Scholar
43 Reetz M. Sommer K. Eur. J. Org. Chem. 2003, 3485

Google Scholar
44 Shi Z. He C. J. Am. Chem. Soc. 2004, 126: 13569

Google Scholar
45 Li Z. Capretto DA. Rahaman RO. He C. J. Am. Chem. Soc. 2007, 129: 12058

Crossref Google Scholar
46 Gu L. Neo BS. Zhang Y. Org. Lett. 2011, 13: 1872

Crossref Google Scholar
47 Mo F. Yan JM. Qui D. Li F. Zhang Y. Wang J. Angew. Chem. Int. Ed. 2010, 49: 2028

Crossref Google Scholar
48 Lu P. Boorman TC. Slawin AMZ. Larrosa I. J. Am. Chem. Soc. 2010, 132: 5580

Crossref PubMed Google Scholar
49 Gaillard S. Slawin AMZ. Nolan SP. Chem. Commun. 2010, 46: 2742

Google Scholar
50 Boogaerts IIF. Nolan SP. J. Am. Chem. Soc. 2010, 132: 8858

Google Scholar
51 Bergman RG. Nature 2007, 446: 391

Crossref PubMed Google Scholar
52 Crabtree RH. J. Organomet. Chem. 2004, 689: 4083

Crossref Google Scholar
53a Jones C. Taube D. Ziatdinov VR. Periana RA. Nielsen RJ. Oxgaard J. Goddard WA. Angew. Chem. Int. Ed. 2004, 43: 4626

Google Scholar
53b De Vos DE. Sels BF. Angew. Chem. Int. Ed. 2005, 44: 30

Google Scholar
54 Hashmi ASK. Schäfer S. Wölfle M. Diez Gil C. Fischer P. Laguna A. Blanco MC. Gimeno MC. Angew. Chem. Int. Ed. 2007, 46: 6184

Crossref Google Scholar
For metal-catalyzed carbene insertion on C-H bonds see selected reviews:
55a Davies HML. Beckwith REJ. Chem. Rev. 2003, 103: 2861

Google Scholar
55b Doyle MP. Duffy R. Ratnikov M. Zhou L. Chem. Rev. 2010, 110: 704

Google Scholar
55c Díaz-Requejo MM. Belderrain TR. Nicasio MC. Pérez PJ. Dalton Trans. 2006, 5559

Google Scholar
56a Fructos MR. Belderrain TR. de Frémont P. Scott NM. Nolan SP. Díaz-Requejo MM. Pérez PJ. Angew. Chem. Int. Ed. 2005, 44: 5284

Google Scholar
56b Fructos MR. de Frémont P. Nolan PSP. Díaz-Requejo MM. Pérez PJ. Organometallics 2006, 25: 2237

Google Scholar
56c Rivilla I. Gómez-Emeterio BP. Fructos MR. Díaz-Requejo MM. Pérez PJ. Organometallics 2011, 30: 2855

Google Scholar
57a Horino Y. Yamamoto T. Ueda K. Kuroda S. Toste FD. J. Am. Chem. Soc. 2009, 131: 2809

Google Scholar
57b Liu Y. Zhang D. Zhou J. Liu C. J. Phys. Chem. A. 2010, 114: 6164

Google Scholar
58 Lemire G. Gandon V. Cariou K. Hours A. Fukuyama T. Dhimane A.-L. Fensterbank L. Malacria M. J. Am. Chem. Soc. 2009, 131: 2993

Crossref Google Scholar
59 Escribano-Cuesta A. López-Carrillo V. Janssen D. Echavarren AM. Chem. Eur. J. 2009, 15: 5646

Crossref Google Scholar

25

Dppf: 1,10-bis(diphenylphosphino)ferrocene.

36

An alternative mechanism in which gold acts as a Lewis acid activating the alkyne in the iodonium species triggering the attack of the heteroaromatic followed by β-elimination cannot be excluded.