8. Fernández I (2018) Energy decomposition analysis and related methods. In: Tantillo D
(ed) Applied theoretical organic chemistry. World Scientific, Hackensack, pp 191–226
9. Mitoraj M, Michalak A (2007) Natural orbitals for chemical valence as descriptors of chemical
bonding in transition metal complexes. J Mol Model 13:347–355
10. Mitoraj MP, Michalak A, Ziegler T (2009) A combined charge and energy decomposition
scheme for bond analysis. J Chem Theory Comput 5:962–975
11. Bleeke JR (2001) Metallabenzenes. Chem Rev 101:1205–1228
12. Landorf CW, Haley MM (2006) Recent advances in metallabenzene chemistry. Angew Chem
Int Ed 45:3914–3936
13. Dalebrook AF, Wright LJ (2012) Anthony FH, Mark JF (eds) Advances in organometallic
chemistry, vol 60. Academic Press, New York, pp 93–177
14. Fernández I, Frenking G, Merino G (2015) Aromaticity of metallabenzenes and related compounds. Chem Soc Rev 44:6452–6463
15. Elliott GP, Roper WR, Waters JM (1982) Metallacyclohexatrienes or ‘metallabenzenes’.
Synthesis of osmabenzene derivatives and X-ray crystal structure of [Os(CSCHCHCHCH)
(CO)(PPh 3 ) 2 ]. J Chem Soc Chem Commun:811–813
16. Frogley BJ, Wright LJ (2014) Fused-ring metallabenzenes. Coord Chem Rev
270–271:151–166
17. Han F, Wang T, Li J, Zhang H, Xia H (2014) m-Metallaphenol: synthesis and reactivity studies.
Chem Eur J 20:4363–4372
18. Zhuo Q, Chen Z, Yang Y, Zhou X, Han F, Zhu J, Zhang H, Xia H (2016) Synthesis of aromatic
ruthenabenzothiophenes via C–H activation of thiophenes. Dalton Trans 45:913–917
19. Zhuo Q, Zhou X, Kang H, Chen Z, Yang Y, Han F, Zhang H, Xia H (2016) Synthesis of fused
metallaaromatics via intramolecular C–H activation of thiophenes. Organometallics
35:1497–1504
20. Frogley BJ, Wright LJ (2016) A metallaanthracene and derived metallaanthraquinone. Angew
Chem Int Ed 56:143–147
21. Atherton JCC, Jones S (2013) Diels–Alder reactions of anthracene, 9-substituted anthracenes
and 9,10-disubstituted anthracenes. Tetrahedron 59:9039–9057
22. García-Rodeja Y, Fernández I (2017) Influence of the transition-metal fragment on the reactivity of metallaanthracenes. Chem Eur J 23:6634–6642
23. García-Melchor M, Braga AAC, Lledós A, Ujaque G, Maseras F (2013) Computational
perspective on Pd-catalyzed C–C cross-coupling reaction mechanisms. Acc Chem Res
46:2626–2634, and references therein
24. Besora M, Gourlaouen C, Yates B, Maseras F (2011) Phosphine and solvent effects on
oxidative addition of CH 3 Br to Pd(PR 3 ) and Pd(PR 3 ) 2 complexes. Dalton Trans
40:11089–11094
25. Besora M, Maseras F (2019) The diverse mechanisms for the oxidative addition of C–Br bonds
to Pd(PR 3 ) and Pd(PR 3 ) 2 complexes. Dalton Trans 48:16242–16248
26. de Jong GT, Bickelhaupt FM (2007) Catalytic carbonÀhalogen bond activation: trends in
reactivity, selectivity, and solvation. J Chem Theory Comput 3:514–529
27. de Jong GT, Bickelhaupt FM (2007) Transition-state energy and position along the reaction
coordinate in an extended activation strain model. ChemPhysChem 8:1170–1181
28. Vermeeren P, Sun X, Bickelhaupt FM (2018) Arylic C–X bond activation by palladium
catalysts: activation strain analyses of reactivity trends. Sci Rep 8:10729
29. Sun X, Rocha MVJ, Hamlin TA, Poater J, Bickelhaupt FM (2019) Understanding the differences between iron and palladium in cross-coupling. Phys Chem Chem Phys 21:9651–9664
30. Joost M, Gualco P, Coppel Y, Miqueu K, Kefalidis CE, Maron L, Amgoune A, Bourissou D
(2014) Direct evidence for intermolecular oxidative addition of σ(Si–Si) bonds to gold. Angew
Chem Int Ed 53:747–751, and references therein
31. Livendahl M, Goehry C, Maseras F, Echavarren AM (2014) Rationale for the sluggish
oxidative addition of aryl halides to Au(I). Chem Commun 50:1533–1536
128
I. Fernández
(ed) Applied theoretical organic chemistry. World Scientific, Hackensack, pp 191–226
9. Mitoraj M, Michalak A (2007) Natural orbitals for chemical valence as descriptors of chemical
bonding in transition metal complexes. J Mol Model 13:347–355
10. Mitoraj MP, Michalak A, Ziegler T (2009) A combined charge and energy decomposition
scheme for bond analysis. J Chem Theory Comput 5:962–975
11. Bleeke JR (2001) Metallabenzenes. Chem Rev 101:1205–1228
12. Landorf CW, Haley MM (2006) Recent advances in metallabenzene chemistry. Angew Chem
Int Ed 45:3914–3936
13. Dalebrook AF, Wright LJ (2012) Anthony FH, Mark JF (eds) Advances in organometallic
chemistry, vol 60. Academic Press, New York, pp 93–177
14. Fernández I, Frenking G, Merino G (2015) Aromaticity of metallabenzenes and related compounds. Chem Soc Rev 44:6452–6463
15. Elliott GP, Roper WR, Waters JM (1982) Metallacyclohexatrienes or ‘metallabenzenes’.
Synthesis of osmabenzene derivatives and X-ray crystal structure of [Os(CSCHCHCHCH)
(CO)(PPh 3 ) 2 ]. J Chem Soc Chem Commun:811–813
16. Frogley BJ, Wright LJ (2014) Fused-ring metallabenzenes. Coord Chem Rev
270–271:151–166
17. Han F, Wang T, Li J, Zhang H, Xia H (2014) m-Metallaphenol: synthesis and reactivity studies.
Chem Eur J 20:4363–4372
18. Zhuo Q, Chen Z, Yang Y, Zhou X, Han F, Zhu J, Zhang H, Xia H (2016) Synthesis of aromatic
ruthenabenzothiophenes via C–H activation of thiophenes. Dalton Trans 45:913–917
19. Zhuo Q, Zhou X, Kang H, Chen Z, Yang Y, Han F, Zhang H, Xia H (2016) Synthesis of fused
metallaaromatics via intramolecular C–H activation of thiophenes. Organometallics
35:1497–1504
20. Frogley BJ, Wright LJ (2016) A metallaanthracene and derived metallaanthraquinone. Angew
Chem Int Ed 56:143–147
21. Atherton JCC, Jones S (2013) Diels–Alder reactions of anthracene, 9-substituted anthracenes
and 9,10-disubstituted anthracenes. Tetrahedron 59:9039–9057
22. García-Rodeja Y, Fernández I (2017) Influence of the transition-metal fragment on the reactivity of metallaanthracenes. Chem Eur J 23:6634–6642
23. García-Melchor M, Braga AAC, Lledós A, Ujaque G, Maseras F (2013) Computational
perspective on Pd-catalyzed C–C cross-coupling reaction mechanisms. Acc Chem Res
46:2626–2634, and references therein
24. Besora M, Gourlaouen C, Yates B, Maseras F (2011) Phosphine and solvent effects on
oxidative addition of CH 3 Br to Pd(PR 3 ) and Pd(PR 3 ) 2 complexes. Dalton Trans
40:11089–11094
25. Besora M, Maseras F (2019) The diverse mechanisms for the oxidative addition of C–Br bonds
to Pd(PR 3 ) and Pd(PR 3 ) 2 complexes. Dalton Trans 48:16242–16248
26. de Jong GT, Bickelhaupt FM (2007) Catalytic carbonÀhalogen bond activation: trends in
reactivity, selectivity, and solvation. J Chem Theory Comput 3:514–529
27. de Jong GT, Bickelhaupt FM (2007) Transition-state energy and position along the reaction
coordinate in an extended activation strain model. ChemPhysChem 8:1170–1181
28. Vermeeren P, Sun X, Bickelhaupt FM (2018) Arylic C–X bond activation by palladium
catalysts: activation strain analyses of reactivity trends. Sci Rep 8:10729
29. Sun X, Rocha MVJ, Hamlin TA, Poater J, Bickelhaupt FM (2019) Understanding the differences between iron and palladium in cross-coupling. Phys Chem Chem Phys 21:9651–9664
30. Joost M, Gualco P, Coppel Y, Miqueu K, Kefalidis CE, Maron L, Amgoune A, Bourissou D
(2014) Direct evidence for intermolecular oxidative addition of σ(Si–Si) bonds to gold. Angew
Chem Int Ed 53:747–751, and references therein
31. Livendahl M, Goehry C, Maseras F, Echavarren AM (2014) Rationale for the sluggish
oxidative addition of aryl halides to Au(I). Chem Commun 50:1533–1536
128
I. Fernández