32. Fernández I, Wolters LP, Bickelhaupt FM (2014) Controlling the oxidative addition of aryl
halides to Au(I). J Comput Chem 35:2140–2145
33. Joost M, Zeineddine A, Estévez L, Mallet-Ladeira S, Miqueu K, Amgoune A, Bourissou D
(2014) Facile oxidative addition of aryl iodides to gold(I) by ligand design: bending turns on
reactivity. J Am Chem Soc 136:14654–14657
34. Alcarazo M (2014) α-Cationic phosphines: synthesis and applications. Chem Eur J
20:7868–7877
35. Alcarazo M (2016) Synthesis, structure, and applications of α-cationic phosphines. Acc Chem
Res 49:1797–1805
36. Petuškova J, Bruns H, Alcarazo M (2011) Cyclopropenylylidene-stabilized diaryl and dialkyl
phosphenium cations: applications in homogeneous gold catalysis. Angew Chem Int Ed
50:3799–3802
37. Petuškova J, Patil M, Holle S, Lehmann CW, Thiel W, Alcarazo M (2011) Synthesis, structure,
and reactivity of carbene-stabilized phosphorus(III)-centered trications [L 3 P]
3+ . J Am Chem
Soc 133:20758–20760
38. García-Rodeja Y, Fernández I (2017) Understanding the effect of α-cationic phosphines and
group 15 analogues on π-acid catalysis. Organometallics 36:460–466
39. Müller TE, Hultzsch KC, Yus M, Foubelo F, Tada M (2008) Hydroamination: direct addition of
amines to alkenes and alkynes. Chem Rev 108:3795–3892
40. Reznichenko AL, Hultzsch KC (2015) Hydroamination of alkenes. Org React 88:1–554
41. Zhang J, Yang CG, He C (2016) Gold(I)-catalyzed intra- and intermolecular hydroamination of
unactivated olefins. J Am Chem Soc 128:1798–1799
42. Giner X, Nájera C (2008) (Triphenyl phosphite)gold(I)-catalyzed intermolecular
hydroamination of alkenes and 1,3-dienes. Org Lett 10:2919–2922
43. Zhang X, Corma A (2008) Efficient addition of alcohols, amines and phenol to unactivated
alkenes by Au(III) or Pd(II) stabilized by CuCl 2 . Dalton Trans 3:397–403
44. Timmerman JC, Laulhé S, Widenhoefer RA (2017) Gold(I)-catalyzed intramolecular
hydroamination of unactivated terminal and internal alkenes with 2-pyridones. Org Lett
19:1466–1469
45. Abadie MA, Trivelli X, Medina F, Duhal M, Kouach M, Linden B, Génin E, Vandewalle M,
Capet F, Roussel P, Del Rosal I, Maron L, Agbossou-Niedercorn F, Michon C (2017) Gold(I)catalysed asymmetric hydroamination of alkenes: a silver- and solvent-dependent
enantiodivergent reaction. Chem Eur J 23:10777–10788
46. Timmerman JC, Robertson BD, Widenhoefer RA (2015) Gold-catalyzed intermolecular antiMarkovnikov hydroamination of alkylidenecyclopropanes. Angew Chem Int Ed 54:2251–2254
47. Zhang Z, Lee SD, Widenhoefer RA (2009) Intermolecular hydroamination of ethylene and
1-alkenes with cyclic ureas catalyzed by achiral and chiral gold(I) complexes. J Am Chem Soc
131:5372–5373
48. Couce-Ríos A, Lledós A, Fernández I, Ujaque G (2019) Origin of the anti-Markovnikov
hydroamination of alkenes catalyzed by L-Au(I) complexes: coordination mode determines
regioselectivity. ACS Catal 9:848–858
49. Fernández I, Bickelhaupt FM, Cossío FP (2012) Type-I dyotropic reactions: understanding
trends in barriers. Chem Eur J 18:12395–12403
50. Fernández I, Bickelhaupt FM, Cossío FP (2014) Ene-ene-yne reactions: activation strain
analysis and the role of aromaticity. Chem Eur J 20:10791–10801
51. O’Reilly ME, Dutta S, Veige AS (2016) β-Alkyl elimination: fundamental principles and some
applications. Chem Rev 116:8105–8145
52. Stockland RA, Jordan RF (2000) Reaction of vinyl chloride with a prototypical metallocene
catalyst: stoichiometric insertion and β-Cl elimination reactions with rac-(EBI)ZrMe
+ and
catalytic dechlorination/oligomerization to oligopropylene by rac-(EBI)ZrMe 2 /MAO. J Am
Chem Soc 122:6315–6316
53. Stockland RA, Foley SR, Jordan RF (2003) Reaction of vinyl chloride with group 4 metal olefin
polymerization catalysts. J Am Chem Soc 125:796–809
A Quantitative Approach to Understanding Reactivity in Organometallic Chemistry
129
halides to Au(I). J Comput Chem 35:2140–2145
33. Joost M, Zeineddine A, Estévez L, Mallet-Ladeira S, Miqueu K, Amgoune A, Bourissou D
(2014) Facile oxidative addition of aryl iodides to gold(I) by ligand design: bending turns on
reactivity. J Am Chem Soc 136:14654–14657
34. Alcarazo M (2014) α-Cationic phosphines: synthesis and applications. Chem Eur J
20:7868–7877
35. Alcarazo M (2016) Synthesis, structure, and applications of α-cationic phosphines. Acc Chem
Res 49:1797–1805
36. Petuškova J, Bruns H, Alcarazo M (2011) Cyclopropenylylidene-stabilized diaryl and dialkyl
phosphenium cations: applications in homogeneous gold catalysis. Angew Chem Int Ed
50:3799–3802
37. Petuškova J, Patil M, Holle S, Lehmann CW, Thiel W, Alcarazo M (2011) Synthesis, structure,
and reactivity of carbene-stabilized phosphorus(III)-centered trications [L 3 P]
3+ . J Am Chem
Soc 133:20758–20760
38. García-Rodeja Y, Fernández I (2017) Understanding the effect of α-cationic phosphines and
group 15 analogues on π-acid catalysis. Organometallics 36:460–466
39. Müller TE, Hultzsch KC, Yus M, Foubelo F, Tada M (2008) Hydroamination: direct addition of
amines to alkenes and alkynes. Chem Rev 108:3795–3892
40. Reznichenko AL, Hultzsch KC (2015) Hydroamination of alkenes. Org React 88:1–554
41. Zhang J, Yang CG, He C (2016) Gold(I)-catalyzed intra- and intermolecular hydroamination of
unactivated olefins. J Am Chem Soc 128:1798–1799
42. Giner X, Nájera C (2008) (Triphenyl phosphite)gold(I)-catalyzed intermolecular
hydroamination of alkenes and 1,3-dienes. Org Lett 10:2919–2922
43. Zhang X, Corma A (2008) Efficient addition of alcohols, amines and phenol to unactivated
alkenes by Au(III) or Pd(II) stabilized by CuCl 2 . Dalton Trans 3:397–403
44. Timmerman JC, Laulhé S, Widenhoefer RA (2017) Gold(I)-catalyzed intramolecular
hydroamination of unactivated terminal and internal alkenes with 2-pyridones. Org Lett
19:1466–1469
45. Abadie MA, Trivelli X, Medina F, Duhal M, Kouach M, Linden B, Génin E, Vandewalle M,
Capet F, Roussel P, Del Rosal I, Maron L, Agbossou-Niedercorn F, Michon C (2017) Gold(I)catalysed asymmetric hydroamination of alkenes: a silver- and solvent-dependent
enantiodivergent reaction. Chem Eur J 23:10777–10788
46. Timmerman JC, Robertson BD, Widenhoefer RA (2015) Gold-catalyzed intermolecular antiMarkovnikov hydroamination of alkylidenecyclopropanes. Angew Chem Int Ed 54:2251–2254
47. Zhang Z, Lee SD, Widenhoefer RA (2009) Intermolecular hydroamination of ethylene and
1-alkenes with cyclic ureas catalyzed by achiral and chiral gold(I) complexes. J Am Chem Soc
131:5372–5373
48. Couce-Ríos A, Lledós A, Fernández I, Ujaque G (2019) Origin of the anti-Markovnikov
hydroamination of alkenes catalyzed by L-Au(I) complexes: coordination mode determines
regioselectivity. ACS Catal 9:848–858
49. Fernández I, Bickelhaupt FM, Cossío FP (2012) Type-I dyotropic reactions: understanding
trends in barriers. Chem Eur J 18:12395–12403
50. Fernández I, Bickelhaupt FM, Cossío FP (2014) Ene-ene-yne reactions: activation strain
analysis and the role of aromaticity. Chem Eur J 20:10791–10801
51. O’Reilly ME, Dutta S, Veige AS (2016) β-Alkyl elimination: fundamental principles and some
applications. Chem Rev 116:8105–8145
52. Stockland RA, Jordan RF (2000) Reaction of vinyl chloride with a prototypical metallocene
catalyst: stoichiometric insertion and β-Cl elimination reactions with rac-(EBI)ZrMe
+ and
catalytic dechlorination/oligomerization to oligopropylene by rac-(EBI)ZrMe 2 /MAO. J Am
Chem Soc 122:6315–6316
53. Stockland RA, Foley SR, Jordan RF (2003) Reaction of vinyl chloride with group 4 metal olefin
polymerization catalysts. J Am Chem Soc 125:796–809
A Quantitative Approach to Understanding Reactivity in Organometallic Chemistry
129