3 FLP Reduction of Carbon Monoxide and Related Reactions
109
57. Curless LD, Clark ER, Cid J, Del Grosso A, Ingleson MJ (2015) Complete Reductive Cleavage of CO Facilitated by Highly Electrophilic Borocations. Chem Commun
51:10903–10906. https://doi.org/10.1039/C5CC03504J
58. Braunschweig H, Dewhurst RD, Hupp F, Nutz M, Radacki K, Tate CW, Vargas A, Ye Q
(2015) Multiple Complexation of CO and Related Ligands to a Main-Group Element. Nature
522:327–330. https://doi.org/10.1038/nature14489
59. Jin J, Zhou M (2018) Boron Carbonyl Complexes Analogous to Hydrocarbons. Dalton Trans
47:17192–17197. https://doi.org/10.1039/C8DT03236J
60. Katsuma Y, Tsukahara N, Wu L, Lin Z, Yamashita M (2018) Reaction of B 2 (o-tol) 4 with
CO and Isocyanides: Cleavage of the C≡O Triple Bond and Direct C-H Borylations. Angew
Chem Int Ed 57:6109–6114. https://doi.org/10.1002/anie.201800878
61. Edel K, Ishibashi JSA, Liu S-Y, Bettinger HF (2019) Superelectrophilicity of 1,2-Azaborine:
Formation of Xenon and Carbon Monoxide Adducts. Angew Chem Int Ed 58:4061–
4064. https://doi.org/10.1002/anie.201813503
62. Devillard M, de Bruin B, Siegler MA, van der Vlugt JI (2017) Transition-Metal-Free Cleavage
of CO. Chem Eur J 23:13628–13632. https://doi.org/10.1002/chem.201703798
63. Omann L, Qu Z-W, Irran E, Klare HFT, Grimme S, Oestreich M (2018) Electrophilic Formylation of Arenes by Silylium Ion Mediated Activation of Carbon Monoxide. Angew Chem
Int Ed 57:8301–8305. https://doi.org/10.1002/anie.201803181
64. Fuchs J, Irran E, Hrobárik P, Klare HFT, Oestreich M (2019) Si−H Bond Activation with
Bullock’s Cationic Tungsten(II) Catalyst: CO as Cooperating Ligand. J Am Chem Soc
141:18845–18850. https://doi.org/10.1021/jacs.9b10304
65. Ramler J, Poater J, Hirsch F, Ritschel B, Fischer I, Bickelhaupt FM, Lichtenberg C (2019)
Carbon Monoxide Insertion at a Heavy p-Block Element: Unprecedented Formation of
a Cationic Bismuth Carbamoyl. Chem Sci 10:4169–4176. https://doi.org/10.1039/C9SC00
278B
66. Sajid M, Elmer L-M, Rosorius C, Daniliuc CG, Grimme S, Kehr G, Erker G (2013) Facile
Carbon Monoxide Reduction at Intramolecular Frustrated P/B Lewis Pair Templates. Angew
Chem Int Ed 52:2243–2246. https://doi.org/10.1002/anie.201208750
67. Sajid M, Kehr G, Daniliuc CG, Erker G (2013) α−Hydroxymethylation of Pyridines at a
Frustrated Lewis Pair Template. Chem Eur J 21:1454–1457. https://doi.org/10.1002/chem.
201405553
68. Li J, Daniliuc CG, Kehr G, Erker G (2019) Preparation of the Borane (Fmes)BH 2 and its
Utilization in the FLP Reduction of Carbon Monoxide and Carbon Dioxide. Angew Chem
Int Ed 58:6737–6741. https://doi.org/10.1002/anie.201901634. Corrigendum: Li J, Daniliuc
CG, Kehr G, Erker G (2019) Angew Chem Int Ed 58:10785. https://doi.org/10.1002/anie.201
906798
69. Ye K-Y, Bursch M, Qu Z-W, Daniliuc CG, Grimme S, Kehr G, Erker G (2017) Reversible
Formylborane/SO 2 Coupling at a Frustrated Lewis Pair. Chem Commun 53:633–635. https://
doi.org/10.1039/C6CC07071J
70. Wang T, Kehr G, Daniliuc CG, Erker G (2018) Metal-Free Carbonylation Route to a Reactive Borataepoxide System. Organometallics37:1040–1049. https://doi.org/10.1021/acs.org
anomet.8b00035
71. Wang T, Wang L, Daniliuc CG, Samigullin K, Wagner M, Kehr G, Erker G (2017) CO/CO,
CO/NO and NO/NO Coupling at a Hidden Frustrated Lewis Pair Template. Chem Sci 8:2457–
2463. https://doi.org/10.1039/C6SC04459J
72. Hrabie JA, Keefer LK (2002) Chemistry of the Nitric Oxide-Releasing Diazeniumdiolate
(“Nitrosohydroxylamine”) Functional Group and Its Oxygen-Substituted Derivatives. Chem
Rev 102:1135–1154. https://doi.org/10.1021/cr000028t
73. Beaudoin D, Wuest JD (2016) Dimerization of Aromatic C-Nitroso Compounds. Chem Rev
102:1135–1154. https://doi.org/10.1021/cr500520s
74. Ye K-Y, Kehr G, Daniliuc CG, Liu L, Grimme S, Erker G (2016) Coupling of Carbon
Monoxide with Nitrogen Monoxide at a Frustrated Lewis Pair Template. Angew Chem Int
Ed 55:9216–9219. https://doi.org/10.1002/anie.201603760
109
57. Curless LD, Clark ER, Cid J, Del Grosso A, Ingleson MJ (2015) Complete Reductive Cleavage of CO Facilitated by Highly Electrophilic Borocations. Chem Commun
51:10903–10906. https://doi.org/10.1039/C5CC03504J
58. Braunschweig H, Dewhurst RD, Hupp F, Nutz M, Radacki K, Tate CW, Vargas A, Ye Q
(2015) Multiple Complexation of CO and Related Ligands to a Main-Group Element. Nature
522:327–330. https://doi.org/10.1038/nature14489
59. Jin J, Zhou M (2018) Boron Carbonyl Complexes Analogous to Hydrocarbons. Dalton Trans
47:17192–17197. https://doi.org/10.1039/C8DT03236J
60. Katsuma Y, Tsukahara N, Wu L, Lin Z, Yamashita M (2018) Reaction of B 2 (o-tol) 4 with
CO and Isocyanides: Cleavage of the C≡O Triple Bond and Direct C-H Borylations. Angew
Chem Int Ed 57:6109–6114. https://doi.org/10.1002/anie.201800878
61. Edel K, Ishibashi JSA, Liu S-Y, Bettinger HF (2019) Superelectrophilicity of 1,2-Azaborine:
Formation of Xenon and Carbon Monoxide Adducts. Angew Chem Int Ed 58:4061–
4064. https://doi.org/10.1002/anie.201813503
62. Devillard M, de Bruin B, Siegler MA, van der Vlugt JI (2017) Transition-Metal-Free Cleavage
of CO. Chem Eur J 23:13628–13632. https://doi.org/10.1002/chem.201703798
63. Omann L, Qu Z-W, Irran E, Klare HFT, Grimme S, Oestreich M (2018) Electrophilic Formylation of Arenes by Silylium Ion Mediated Activation of Carbon Monoxide. Angew Chem
Int Ed 57:8301–8305. https://doi.org/10.1002/anie.201803181
64. Fuchs J, Irran E, Hrobárik P, Klare HFT, Oestreich M (2019) Si−H Bond Activation with
Bullock’s Cationic Tungsten(II) Catalyst: CO as Cooperating Ligand. J Am Chem Soc
141:18845–18850. https://doi.org/10.1021/jacs.9b10304
65. Ramler J, Poater J, Hirsch F, Ritschel B, Fischer I, Bickelhaupt FM, Lichtenberg C (2019)
Carbon Monoxide Insertion at a Heavy p-Block Element: Unprecedented Formation of
a Cationic Bismuth Carbamoyl. Chem Sci 10:4169–4176. https://doi.org/10.1039/C9SC00
278B
66. Sajid M, Elmer L-M, Rosorius C, Daniliuc CG, Grimme S, Kehr G, Erker G (2013) Facile
Carbon Monoxide Reduction at Intramolecular Frustrated P/B Lewis Pair Templates. Angew
Chem Int Ed 52:2243–2246. https://doi.org/10.1002/anie.201208750
67. Sajid M, Kehr G, Daniliuc CG, Erker G (2013) α−Hydroxymethylation of Pyridines at a
Frustrated Lewis Pair Template. Chem Eur J 21:1454–1457. https://doi.org/10.1002/chem.
201405553
68. Li J, Daniliuc CG, Kehr G, Erker G (2019) Preparation of the Borane (Fmes)BH 2 and its
Utilization in the FLP Reduction of Carbon Monoxide and Carbon Dioxide. Angew Chem
Int Ed 58:6737–6741. https://doi.org/10.1002/anie.201901634. Corrigendum: Li J, Daniliuc
CG, Kehr G, Erker G (2019) Angew Chem Int Ed 58:10785. https://doi.org/10.1002/anie.201
906798
69. Ye K-Y, Bursch M, Qu Z-W, Daniliuc CG, Grimme S, Kehr G, Erker G (2017) Reversible
Formylborane/SO 2 Coupling at a Frustrated Lewis Pair. Chem Commun 53:633–635. https://
doi.org/10.1039/C6CC07071J
70. Wang T, Kehr G, Daniliuc CG, Erker G (2018) Metal-Free Carbonylation Route to a Reactive Borataepoxide System. Organometallics37:1040–1049. https://doi.org/10.1021/acs.org
anomet.8b00035
71. Wang T, Wang L, Daniliuc CG, Samigullin K, Wagner M, Kehr G, Erker G (2017) CO/CO,
CO/NO and NO/NO Coupling at a Hidden Frustrated Lewis Pair Template. Chem Sci 8:2457–
2463. https://doi.org/10.1039/C6SC04459J
72. Hrabie JA, Keefer LK (2002) Chemistry of the Nitric Oxide-Releasing Diazeniumdiolate
(“Nitrosohydroxylamine”) Functional Group and Its Oxygen-Substituted Derivatives. Chem
Rev 102:1135–1154. https://doi.org/10.1021/cr000028t
73. Beaudoin D, Wuest JD (2016) Dimerization of Aromatic C-Nitroso Compounds. Chem Rev
102:1135–1154. https://doi.org/10.1021/cr500520s
74. Ye K-Y, Kehr G, Daniliuc CG, Liu L, Grimme S, Erker G (2016) Coupling of Carbon
Monoxide with Nitrogen Monoxide at a Frustrated Lewis Pair Template. Angew Chem Int
Ed 55:9216–9219. https://doi.org/10.1002/anie.201603760