L-proline chiral auxiliaries: mer η
3
-N,C,N versus square planar η
4
-N,C,N,O coordination.
Tetrahedron Asymmetry 17:674–686. https://doi.org/10.1016/j.tetasy.2005.12.040
64. Gosiewska S, Martinez Herreras S, Lutz M, Spek AL, Havenith RWA, van Klink GPM, van
Koten G, Klein Gebbink RJM (2008) Synthesis, structure, and catalytic performance of
diastereopure five-coordinated NCN-pincer palladium(II) complexes bearing bulky amino
acid substituents. Organometallics 27(11):2549–2559. https://doi.org/10.1021/om701261q
65. Holz J, Sturmer R, Schmidt U, Drexler H-J, Heller D, Krimmer H-P, Borner A (2001)
Synthesis of chiral 2,5-bis(oxymethyl)-functionalized bis(phospholanes) and their application
in Rh- and Ru-catalyzed enantioselective hydrogenations. Eur J Org Chem 24:4615–4624.
https://doi.org/10.1002/1099-0690(200112)2001:24<4615::AID-EJOC4615>3.0.CO;2-N
66. Borner A (2001) The effect of internal hydroxy groups in chiral diphosphane rhodium(I)
catalysts on the asymmetric hydrogenation of functionalized olefins. Eur J Inorg Chem
2:327–337. https://doi.org/10.1002/1099-0682(200102)2001:2<327::AID-EJIC327>3.0.
CO;2-A
67. Jia X, Zhang L, Qin C, Leng X, Huang Z (2014) Iridium complexes of new NCP pincer
ligands: catalytic alkane dehydrogenation and alkene isomerization. Chem Commun 50
(75):11056–11059. https://doi.org/10.1039/C3CC46851H
68. Wang Y, Qin C, Jia X, Leng X, Huang Z (2017) An Agostic iridium pincer complex as a
highly efficient and selective catalyst for monoisomerization of 1-alkenes to trans-2-alkenes.
Angew Chem Int Ed 56(6):1614–1618. https://doi.org/10.1002/anie.201611007
69. Kita MR, Miller AJM (2014) Cation-modulated reactivity of iridium hydride pincer-crown
ether complexes. J Am Chem Soc 136(41):14519–14529. https://doi.org/10.1021/ja507324s
70. Smith JB, Kerr SH, White PS, Miller AJM (2017) Thermodynamic studies of cationmacrocycle interactions in nickel pincer-crown ether complexes enable switchable ligation.
Organometallics 36(16):3094–3103. https://doi.org/10.1021/acs.organomet.7b00431
71. Camp AM, Kita MR, Grajeda J, White PS, Dickie DA, Miller AJM (2017) Mapping the
binding modes of hemilabile pincer-crown ether ligands in solution using diamagnetic anisotropic effects on NMR chemical shift. Inorg Chem 56(18):11141–11150. https://doi.org/10.
1021/acs.inorgchem.7b01485
72. Grajeda J, Kita MR, Gregor LC, White PS, Miller AJM (2016) Diverse cation-promoted
reactivity of iridium carbonyl pincer-crown ether complexes. Organometallics 35(3):306–316.
https://doi.org/10.1021/acs.organomet.5b00786
73. Kita MR, Miller AJM (2017) An ion-responsive pincer-crown ether catalyst system for rapid
and switchable olefin isomerization. Angew Chem Int Ed 56(20):5498–5502. https://doi.org/
10.1002/anie.201701006
74. Lesueur W, Solari E, Floriani C, Chiesi-Villa A, Rizzoli C (1997) A bidentate bisphosphine
functioning in intramolecular aliphatic metalation and as an NMR spectroscopic probe for the
metal coordination environment. Inorg Chem 36:3354–3362. https://doi.org/10.1021/
ic9700819
75. Weng W, Parkin S, Ozerov OV (2006) Double C-H activation results in ruthenium complexes
of a neutral PCP ligand with a central carbene moiety. Organometallics 25:5345–5354. https://
doi.org/10.1021/om060464r
76. Gelman D, Musa S (2012) Coordination versatility of sp
3
-hybridized pincer ligands toward
ligand-metal cooperative catalysis. ACS Catal 2:2456–2466. https://doi.org/10.1021/
cs3005083
77. Cohen S, Borin V, Schapiro I, Musa S, De-Botton S, Belkova NV, Gelman D (2017) Ir(III)PC(sp
3
)P bifunctional catalysts for production of H 2 by dehydrogenation of formic acid:
experimental and theoretical study. ACS Catal 7(12):8139–8146. https://doi.org/10.1021/
acscatal.7b02482
78. Musa S, Shaposhnikov I, Cohen S, Gelman D (2011) Ligand-metal cooperation in PCP pincer
complexes: rational design and catalytic activity in acceptorless dehydrogenation of alcohols.
Angew Chem Int Ed 50:3533–3537. https://doi.org/10.1002/anie.201007367
Cooperative Reactivity by Pincer-Type Complexes Possessing Secondary. . .
131
3
-N,C,N versus square planar η
4
-N,C,N,O coordination.
Tetrahedron Asymmetry 17:674–686. https://doi.org/10.1016/j.tetasy.2005.12.040
64. Gosiewska S, Martinez Herreras S, Lutz M, Spek AL, Havenith RWA, van Klink GPM, van
Koten G, Klein Gebbink RJM (2008) Synthesis, structure, and catalytic performance of
diastereopure five-coordinated NCN-pincer palladium(II) complexes bearing bulky amino
acid substituents. Organometallics 27(11):2549–2559. https://doi.org/10.1021/om701261q
65. Holz J, Sturmer R, Schmidt U, Drexler H-J, Heller D, Krimmer H-P, Borner A (2001)
Synthesis of chiral 2,5-bis(oxymethyl)-functionalized bis(phospholanes) and their application
in Rh- and Ru-catalyzed enantioselective hydrogenations. Eur J Org Chem 24:4615–4624.
https://doi.org/10.1002/1099-0690(200112)2001:24<4615::AID-EJOC4615>3.0.CO;2-N
66. Borner A (2001) The effect of internal hydroxy groups in chiral diphosphane rhodium(I)
catalysts on the asymmetric hydrogenation of functionalized olefins. Eur J Inorg Chem
2:327–337. https://doi.org/10.1002/1099-0682(200102)2001:2<327::AID-EJIC327>3.0.
CO;2-A
67. Jia X, Zhang L, Qin C, Leng X, Huang Z (2014) Iridium complexes of new NCP pincer
ligands: catalytic alkane dehydrogenation and alkene isomerization. Chem Commun 50
(75):11056–11059. https://doi.org/10.1039/C3CC46851H
68. Wang Y, Qin C, Jia X, Leng X, Huang Z (2017) An Agostic iridium pincer complex as a
highly efficient and selective catalyst for monoisomerization of 1-alkenes to trans-2-alkenes.
Angew Chem Int Ed 56(6):1614–1618. https://doi.org/10.1002/anie.201611007
69. Kita MR, Miller AJM (2014) Cation-modulated reactivity of iridium hydride pincer-crown
ether complexes. J Am Chem Soc 136(41):14519–14529. https://doi.org/10.1021/ja507324s
70. Smith JB, Kerr SH, White PS, Miller AJM (2017) Thermodynamic studies of cationmacrocycle interactions in nickel pincer-crown ether complexes enable switchable ligation.
Organometallics 36(16):3094–3103. https://doi.org/10.1021/acs.organomet.7b00431
71. Camp AM, Kita MR, Grajeda J, White PS, Dickie DA, Miller AJM (2017) Mapping the
binding modes of hemilabile pincer-crown ether ligands in solution using diamagnetic anisotropic effects on NMR chemical shift. Inorg Chem 56(18):11141–11150. https://doi.org/10.
1021/acs.inorgchem.7b01485
72. Grajeda J, Kita MR, Gregor LC, White PS, Miller AJM (2016) Diverse cation-promoted
reactivity of iridium carbonyl pincer-crown ether complexes. Organometallics 35(3):306–316.
https://doi.org/10.1021/acs.organomet.5b00786
73. Kita MR, Miller AJM (2017) An ion-responsive pincer-crown ether catalyst system for rapid
and switchable olefin isomerization. Angew Chem Int Ed 56(20):5498–5502. https://doi.org/
10.1002/anie.201701006
74. Lesueur W, Solari E, Floriani C, Chiesi-Villa A, Rizzoli C (1997) A bidentate bisphosphine
functioning in intramolecular aliphatic metalation and as an NMR spectroscopic probe for the
metal coordination environment. Inorg Chem 36:3354–3362. https://doi.org/10.1021/
ic9700819
75. Weng W, Parkin S, Ozerov OV (2006) Double C-H activation results in ruthenium complexes
of a neutral PCP ligand with a central carbene moiety. Organometallics 25:5345–5354. https://
doi.org/10.1021/om060464r
76. Gelman D, Musa S (2012) Coordination versatility of sp
3
-hybridized pincer ligands toward
ligand-metal cooperative catalysis. ACS Catal 2:2456–2466. https://doi.org/10.1021/
cs3005083
77. Cohen S, Borin V, Schapiro I, Musa S, De-Botton S, Belkova NV, Gelman D (2017) Ir(III)PC(sp
3
)P bifunctional catalysts for production of H 2 by dehydrogenation of formic acid:
experimental and theoretical study. ACS Catal 7(12):8139–8146. https://doi.org/10.1021/
acscatal.7b02482
78. Musa S, Shaposhnikov I, Cohen S, Gelman D (2011) Ligand-metal cooperation in PCP pincer
complexes: rational design and catalytic activity in acceptorless dehydrogenation of alcohols.
Angew Chem Int Ed 50:3533–3537. https://doi.org/10.1002/anie.201007367
Cooperative Reactivity by Pincer-Type Complexes Possessing Secondary. . .
131