44. Zhu Z-H, Li Y, Wang Y-B, Lan Z-G, Zhu X, Hao X-Q, Song M-P (2019) α-Alkylation of
nitriles with alcohols catalyzed by NNN
0 pincer Ru(II) complexes bearing bipyridyl
imidazoline ligands. Organometallics 38:2156–2166
45. Chakraborty S, Das UK, Ben-David Y, Milstein D (2017) Manganese catalyzed alphaolefination of nitriles by primary alcohols. J Am Chem Soc 139:11710–11713
46. Thiyagarajan S, Gunanathan C (2018) Ruthenium-catalyzed α-olefination of nitriles using
secondary alcohols. ACS Catal 8:2473–2478
47. Luque-Urrutia JA, Sola M, Milstein D, Poater A (2019) Mechanism of the manganese-pincercatalyzed acceptorless dehydrogenative coupling of nitriles and alcohols. J Am Chem Soc
141:2398–2403
48. Yadav V, Landge VG, Subaramanian M, Balaraman E (2020) Manganese-catalyzed alphaolefination of nitriles with secondary alcohols. ACS Catal 10:947–954
49. Nerush A, Vogt M, Gellrich U, Leitus G, Ben-David Y, Milstein D (2016) Template catalysis
by metal-ligand cooperation. C-C bond formation via conjugate addition of non-activated
nitriles under mild, base-free conditions catalyzed by a manganese pincer complex. J Am
Chem Soc 138:6985–6997
50. Tang S, von Wolff N, Diskin-Posner Y, Leitus G, Ben-David Y, Milstein D (2019) Pyridinebased PCP-ruthenium complexes: unusual structures and metal-ligand cooperation. J Am
Chem Soc 141:7554–7561
51. Krishnakumar V, Gunanathan C (2018) Ruthenium-catalyzed selective alpha-deuteration of
aliphatic nitriles using D 2 O. Chem Commun 54:8705–8708
52. Huo RP, Zhang X, Zhang CF, Li XX (2019) Computational insight into the mechanism of
ruthenium(II)catalyzed alpha-alkylation of arylmethyl nitriles using alcohols. J Phys Chem A
123:10263–10272
53. Hale LVA, Sikes NM, Szymczak NK (2019) Reductive C-C coupling from alpha,betaunsaturated nitriles by intercepting keteniminates. Angew Chem Int Ed 58:8531–8535
54. Fan L, Ozerov OV (2005) Efficient nickel catalyst for coupling of acetonitrile with aldehydes.
Chem Commun:4450–4452
55. Aydin J, Conrad CS, Szabó KJ (2008) Stereoselective pincer-complex catalyzed C-H
functionalization of benzyl nitriles under mild conditions. An efficient route to
β-aminonitriles. Org Lett 10:5175–5178
56. Aydin J, Szabó KJ (2008) Palladium-pincer complex catalyzed C-C coupling of allyl nitriles
with tosyl imines via regioselective allylic C-H bond functionalization. Org Lett
10:2881–2884
57. Rani V, Singh HB, Butcher RJ (2018) Protic and substituted NCN palladium(II) pincer
complexes with 1,3-bis(benzimidazol-2
0 -yl)-2-bromobenzenes: structure and catalysis. J
Organomet Chem 859:33–43
58. Stark MA, Richards CJ (1997) Synthesis and application of cationic 2,6-Bis(2-oxazolinyl)
phenylpalladium(ll) complexes. Tetrahedron Lett 38:5881–5884
59. Stark MA, Jones G, Richards CJ (2000) Cationic [2,6-Bis(2
0 -oxazolinyl)phenyl]palladium
(II) complexes: catalysts for the asymmetric michael reaction. Organometallics 19:1282–1291
60. Motoyama Y, Koga Y, Kobayashi K, Aoki K, Nishiyama H (2002) Novel asymmetric michael
addition of cyanopropionates to acrolein by the use of a bis(oxazolinyl)phenylstannanederived rhodium(III) complex as a chiral Lewis acid catalyst. Chem Eur J 8:2968–2975
61. Takenaka K, Minakawa M, Uozumi Y (2005) NCN pincer palladium complexes: their
preparation via a ligand introduction route and their catalytic properties. J Am Chem Soc
127:12273–12281
62. Mazet C, Gade LH (2003) Double bonds in motion: bis(oxazolinylmethyl)pyrroles and their
metal-induced planarization to a new class of rigid chiral C2-symmetric complexes. Chem Eur
J 9:1759–1767
63. Arai T, Oka I, Morihata T, Awata A, Masu H (2013) A neutral, chiral, bis(imidazolidine)derived NCN-type palladium pincer complex with catalytic activity. Chem Eur J
19:1554–1557
Catalytic Conversion of Nitriles by Metal Pincer Complexes
375
nitriles with alcohols catalyzed by NNN
0 pincer Ru(II) complexes bearing bipyridyl
imidazoline ligands. Organometallics 38:2156–2166
45. Chakraborty S, Das UK, Ben-David Y, Milstein D (2017) Manganese catalyzed alphaolefination of nitriles by primary alcohols. J Am Chem Soc 139:11710–11713
46. Thiyagarajan S, Gunanathan C (2018) Ruthenium-catalyzed α-olefination of nitriles using
secondary alcohols. ACS Catal 8:2473–2478
47. Luque-Urrutia JA, Sola M, Milstein D, Poater A (2019) Mechanism of the manganese-pincercatalyzed acceptorless dehydrogenative coupling of nitriles and alcohols. J Am Chem Soc
141:2398–2403
48. Yadav V, Landge VG, Subaramanian M, Balaraman E (2020) Manganese-catalyzed alphaolefination of nitriles with secondary alcohols. ACS Catal 10:947–954
49. Nerush A, Vogt M, Gellrich U, Leitus G, Ben-David Y, Milstein D (2016) Template catalysis
by metal-ligand cooperation. C-C bond formation via conjugate addition of non-activated
nitriles under mild, base-free conditions catalyzed by a manganese pincer complex. J Am
Chem Soc 138:6985–6997
50. Tang S, von Wolff N, Diskin-Posner Y, Leitus G, Ben-David Y, Milstein D (2019) Pyridinebased PCP-ruthenium complexes: unusual structures and metal-ligand cooperation. J Am
Chem Soc 141:7554–7561
51. Krishnakumar V, Gunanathan C (2018) Ruthenium-catalyzed selective alpha-deuteration of
aliphatic nitriles using D 2 O. Chem Commun 54:8705–8708
52. Huo RP, Zhang X, Zhang CF, Li XX (2019) Computational insight into the mechanism of
ruthenium(II)catalyzed alpha-alkylation of arylmethyl nitriles using alcohols. J Phys Chem A
123:10263–10272
53. Hale LVA, Sikes NM, Szymczak NK (2019) Reductive C-C coupling from alpha,betaunsaturated nitriles by intercepting keteniminates. Angew Chem Int Ed 58:8531–8535
54. Fan L, Ozerov OV (2005) Efficient nickel catalyst for coupling of acetonitrile with aldehydes.
Chem Commun:4450–4452
55. Aydin J, Conrad CS, Szabó KJ (2008) Stereoselective pincer-complex catalyzed C-H
functionalization of benzyl nitriles under mild conditions. An efficient route to
β-aminonitriles. Org Lett 10:5175–5178
56. Aydin J, Szabó KJ (2008) Palladium-pincer complex catalyzed C-C coupling of allyl nitriles
with tosyl imines via regioselective allylic C-H bond functionalization. Org Lett
10:2881–2884
57. Rani V, Singh HB, Butcher RJ (2018) Protic and substituted NCN palladium(II) pincer
complexes with 1,3-bis(benzimidazol-2
0 -yl)-2-bromobenzenes: structure and catalysis. J
Organomet Chem 859:33–43
58. Stark MA, Richards CJ (1997) Synthesis and application of cationic 2,6-Bis(2-oxazolinyl)
phenylpalladium(ll) complexes. Tetrahedron Lett 38:5881–5884
59. Stark MA, Jones G, Richards CJ (2000) Cationic [2,6-Bis(2
0 -oxazolinyl)phenyl]palladium
(II) complexes: catalysts for the asymmetric michael reaction. Organometallics 19:1282–1291
60. Motoyama Y, Koga Y, Kobayashi K, Aoki K, Nishiyama H (2002) Novel asymmetric michael
addition of cyanopropionates to acrolein by the use of a bis(oxazolinyl)phenylstannanederived rhodium(III) complex as a chiral Lewis acid catalyst. Chem Eur J 8:2968–2975
61. Takenaka K, Minakawa M, Uozumi Y (2005) NCN pincer palladium complexes: their
preparation via a ligand introduction route and their catalytic properties. J Am Chem Soc
127:12273–12281
62. Mazet C, Gade LH (2003) Double bonds in motion: bis(oxazolinylmethyl)pyrroles and their
metal-induced planarization to a new class of rigid chiral C2-symmetric complexes. Chem Eur
J 9:1759–1767
63. Arai T, Oka I, Morihata T, Awata A, Masu H (2013) A neutral, chiral, bis(imidazolidine)derived NCN-type palladium pincer complex with catalytic activity. Chem Eur J
19:1554–1557
Catalytic Conversion of Nitriles by Metal Pincer Complexes
375