Synergistic Bimetallic Catalysis for Carboboration of Unsaturated Hydrocarbons

Eva Rivera-Chao; Laura Fra; Martín Fañanás-Mastral

doi:10.1055/s-0037-1610434

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(19): 3825-3832
DOI: 10.1055/s-0037-1610434

short review

Synergistic Bimetallic Catalysis for Carboboration of Unsaturated Hydrocarbons

Eva Rivera-Chao

Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS), Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain eMail: martin.fananas@usc.es

,

Laura Fra

Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS), Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain eMail: martin.fananas@usc.es

,

Martín Fañanás-Mastral *

Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS), Departamento de Química Orgánica, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain eMail: martin.fananas@usc.es

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Abstract

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Abstract

Synergistic bimetallic catalysis has become a very efficient tool for the selective carboboration of unsaturated hydrocarbons. This synthetic approach is based on the use of a catalytically generated boron-substituted organocopper nucleophile in a cross-coupling reaction catalyzed by a second transition metal. This way, hydrocarbons can be used as pro-nucleophiles in this type of transformations thus rendering a clean and operationally simple alternative to the traditional cross-coupling methodologies. This review provides a summary of the developments on this topic and discusses both the synthetic utility and mechanisms of these reactions.

1 Introduction

2 Carboboration of Alkenes via Synergistic Catalysis

3 Carboboration of 1,3-Dienes via Synergistic Catalysis

4 Carboboration of Alkynes via Synergistic Catalysis

5 Conclusions

Key words

boron - copper - cross-coupling - synergistic catalysis - unsaturated hydrocarbons - palladium - C–C bond formation - C–B bond formation

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Referenzen

References

1a Negishi E. Angew. Chem. Int. Ed. 2011; 50: 6738
1b Johansson Seechurn CC. C. Kitching MO. Colacot TJ. Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062

2a Stille JK. Angew. Chem. Int. Ed. 1986; 25: 508
2b Espinet P. Echavarren AM. Angew. Chem. Int. Ed. 2004; 43: 4704

3a Miyaura N. Suzuki A. Chem. Rev. 1995; 95: 2457
3b Suzuki A. Angew. Chem. Int. Ed. 2011; 50: 6722
3c Shi Y. Jung B. Torker S. Hoveyda AH. J. Am. Chem. Soc. 2015; 137: 8948

4a Knochel P. Singer RD. Chem. Rev. 1993; 93: 2117
4b Phapale VB. Cárdenas DJ. Chem. Soc. Rev. 2009; 38: 1598
4c Kacprzynski MA. May TL. Kazane SA. Hoveyda AH. Angew. Chem. Int. Ed. 2007; 46: 4554

5a Denmark SE. Regens CS. Acc. Chem. Res. 2008; 41: 1486
5b Hiyama T. Nakao Y. Chem. Soc. Rev. 2011; 40: 4893

6a Tamao K. Sumitani K. Kumada M. J. Am. Chem. Soc. 1972; 94: 4374
6b Knappe CE. I. von Wangelin AJ. Chem. Soc. Rev. 2011; 40: 4948
6c Alexakis A. Bäckvall JE. Krause N. Pámies O. Diéguez M. Chem. Rev. 2008; 108: 2796
6d Harutyunyan SR. den Hartog T. Geurts K. Minnaard AJ. Feringa BL. Chem. Rev. 2008; 108: 2824

7a Lee Y. Akiyama K. Gillingham D. Brown MK. Hoveyda AH. J. Am. Chem. Soc. 2008; 130: 446
7b Dabrowski JA. Gao F. Hoveyda AH. J. Am. Chem. Soc. 2011; 133: 4778

8a Murahashi S. Yamamura M. Yanagisawa K. Mita N. Kondo K. J. Org. Chem. 1979; 44: 2408
8b Pérez M. Fañanás-Mastral M. Bos PH. Rudolph A. Harutyunyan SR. Feringa BL. Nat. Chem. 2011; 3: 377
8c Giannerini M. Fañanás-Mastral M. Feringa BL. Nat. Chem. 2013; 5: 667

9a Ito H. Yamanaka H. Tateiwa J. Hosomi A. Tetrahedron Lett. 2000; 41: 6821
9b Takahashi K. Ishiyama T. Miyaura N. J. Organomet. Chem. 2001; 625: 47
9c Laitar DS. Müller P. Sadighi JP. J. Am. Chem. Soc. 2005; 127: 17196

10a Laitar DS. Tsui EY. Sadighi JP. Organometallics 2006; 25: 2405
10b Dang L. Zhao H. Lin Z. Marder TB. Organometallics 2007; 26: 2824
10c Zhang L. Cheng J. Carry B. Hou Z. J. Am. Chem. Soc. 2012; 134: 14314
10d Semba K. Shinomiya M. Fujihara T. Terao J. Tsuji Y. Chem. Eur. J. 2013; 19: 7125

For reviews on the reactivity of borylcopper complexes towards unsaturated compounds, see:

10e Semba K. Fujihara T. Terao J. Tsuji Y. Tetrahedron 2015; 71: 2183
10f Neeve EC. Geier SJ. Mkhalid IA. I. Westcott SA. Marder TB. Chem. Rev. 2016; 116: 9091

For some examples, see:

11a Alfaro R. Parra A. Alemán J. García Ruano JL. Tortosa M. J. Am. Chem. Soc. 2012; 134: 15165
11b Yoshida H. Kageyuki I. Takaki K. Org. Lett. 2013; 15: 952
11c Liu P. Fukui Y. Tian P. He Z.-T. Sun C.-Y. Wu N.-Y. Lin G.-Q. J. Am. Chem. Soc. 2013; 135: 11700
11d Meng F. McGrath KP. Hoveyda AH. Nature 2014; 513: 367
11e Zhou Y. You W. Smith KB. Brown MK. Angew. Chem. Int. Ed. 2014; 53: 3475
11f Su W. Gong T.-J. Lu X. Xu M.-Y. Yu C.-G. Xu Z.-Y. Yu H.-Z. Xiao B. Fu Y. Angew. Chem. Int. Ed. 2015; 54: 12957
11g Bin H.-Y. Wei X. Zi J. Zuo Y.-J. Wang T.-C. Zhong C.-M. ACS Catal. 2015; 5: 6670
11h Itoh T. Shimizu Y. Kanai M. J. Am. Chem. Soc. 2016; 138: 7528
11i Kim N. Han JT. Ryu DH. Yun J. Org. Lett. 2017; 19: 6144
11j Chen B. Cao P. Liao Y. Wang M. Liao J. Org. Lett. 2018; 20: 1346

For pioneering work on cooperative Cu/Pd catalysis, see:

12a Sonogashira K. Tohda Y. Hagihara N. Tetrahedron Lett. 1975; 4467
12b Liebeskind LS. Fengl RW. J. Org. Chem. 1990; 55: 5359

For reviews on synergistic catalysis, see:

12c Allen AE. MacMillan DW. C. Chem. Sci. 2012; 3: 633
12d Pye DR. Mankad NP. Chem. Sci. 2017; 8: 1705
12e Lorion MM. Maindan K. Kapdi AR. Ackermann L. Chem. Soc. Rev. 2017; 46: 7399

For related transformations using CuH/Pd catalysis, see:

13a Semba K. Ariyama K. Zheng H. Kameyama R. Sakaki S. Nakao Y. Angew. Chem. Int. Ed. 2016; 55: 6275
13b Friis SD. Pirnot MT. Buchwald SL. J. Am. Chem. Soc. 2016; 138: 8372
13c Friis SD. Pirnot MT. Dupuis LN. Buchwald SL. Angew. Chem. Int. Ed. 2017; 56: 7242

For carbosilylation processes, see:

13d Vercruysse S. Cornelissen L. Nahra F. Collard L. Riant O. Chem. Eur J. 2014; 20: 1834
13e Shintani R. Kurata H. Nozaki K. J. Org. Chem. 2016; 81: 3065
13f Takeda M. Yabushita K. Yasuda S. Ohmiya H. Chem. Commun. 2018; 54: 6776

For other types of transformations involving synergistic catalysis, see:

13g Goossen L. Deng G. Levy LM. Science 2006; 313: 662
13h Huang J. Chan J. Chen Y. Borths CJ. Baucom KD. Larsen RD. Faul MM. J. Am. Chem. Soc. 2010; 132: 3674
13i Wei L. Xu S.-M. Zhu Q. Che C. Wang C.-J. Angew. Chem. Int. Ed. 2017; 56: 12312

14 Semba K. Nakao Y. J. Am. Chem. Soc. 2014; 136: 7567
15 Smith KB. Logan KM. You W. Brown MK. Chem. Eur. J. 2014; 20: 12032
16 Logan KM. Smith KB. Brown MK. Angew. Chem. Int. Ed. 2015; 54: 5228
17 Logan KM. Brown MK. Angew. Chem. Int. Ed. 2017; 56: 851
18 Chen B. Cao P. Yin X. Liao Y. Jiang L. Ye J. Wang M. Liao J. ACS Catal. 2017; 7: 2425
19 Jia T. Cao P. Wang B. Lou Y. Yin X. Wang M. Liao J. J. Am. Chem. Soc. 2015; 137: 13760
20 Semba K. Ohtagaki Y. Nakao Y. Org. Lett. 2016; 18: 3956
21 Smith KB. Brown MK. J. Am. Chem. Soc. 2017; 139: 7721
22 Sardini SR. Brown MK. J. Am. Chem. Soc. 2017; 139: 9823
23 Semba K. Nakao Y. Bull. Chem. Soc. Jpn. 2017; 90: 1340
24 Lesieur M. Bidal YD. Lazreg F. Nahra F. Cazin CS. J. ChemCatChem 2015; 7: 2108
25 Mateos J. Rivera-Chao E. Fañanás-Mastral M. ACS Catal. 2017; 7: 5340