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jo400741t
145. Boga SB, Alhassan AB, Hesk D (2014) Efficient synthesis of
2
H &
13
C labeled benzaldehydes
via regio-selective formylation. Tetrahedron Lett 55:4442–4444. https://doi.org/10.1016/j.
tetlet.2014.06.053
146. Kerr WJ, Reid M, Tuttle T (2017) Iridium-catalyzed formyl-selective deuteration of aldehydes. Angew Chem Int Ed 56:7808–7812. https://doi.org/10.1002/anie.201702997
147. Fortman GC, Jacobsen H, Cavallo L, Nolan SP (2011) Catalytic deuteration of silanes
mediated by N-heterocyclic carbene-Ir(III) complexes. Chem Commun 47:9723. https://doi.
org/10.1039/c1cc13492b
148. Iluc VM, Fedorov A, Grubbs RH (2012) H/D exchange processes catalyzed by an iridiumpincer complex. Organometallics 31:39–41. https://doi.org/10.1021/om201049p
149. Nelson DJ, Egbert JD, Nolan SP (2013) Deuteration of boranes: catalysed versus
non-catalysed processes. Dalton Trans 42:4105. https://doi.org/10.1039/c3dt33045a
150. Garnett JL, Hodges RJ (1967) Homogeneous metal-catalyzed exchange of aromatic compounds. Isotopic hydrogen labeling procedure. J Am Chem Soc 89:4546–4547. https://doi.org/
10.1021/ja00993a067
151. Lockley WJS (1982) Regioselective deuteration of aromatic and α,β-unsaturated carboxylic
acids via rhodium(III) chloride catalysed exchange with deuterium oxide. Tetrahedron Lett
23:3819–3822. https://doi.org/10.1016/S0040-4039(00)87716-3
152. Anderson GK, Saum SE, Cross RJ, Morris SA (1983) Homogeneous catalysts of hydrogendeuterium exchange reactions involving cyclopentadienyl complexes of palladium and platinum. Organometallics 2:780–782. https://doi.org/10.1021/om00078a021
153. Heys R (1992) Investigation of [IrH 2 (Me 2 CO) 2 (PPh 3 ) 2 ]BF 4 as a catalyst of hydrogen isotope
exchange of substrates in solution. J Chem Soc Chem Commun 680. https://doi.org/10.1039/
c39920000680
154. Maldonado AG, Rothenberg G (2010) Predictive modeling in homogeneous catalysis: a
tutorial. Chem Soc Rev 39:1891–1902. https://doi.org/10.1039/b921393g
155. Houk KN, Cheong PH-Y (2008) Computational prediction of small-molecule catalysts. Nature
455:309–313. https://doi.org/10.1038/nature07368
156. Peng Q, Duarte F, Paton RS (2016) Computing organic stereoselectivity – from concepts to
quantitative calculations and predictions. Chem Soc Rev 45:6093–6107. https://doi.org/10.
1039/c6cs00573j
157. Sperger T, Sanhueza IA, Schoenebeck F (2016) Computation and experiment: a powerful
combination to understand and predict reactivities. Acc Chem Res 49:1311–1319. https://doi.
org/10.1021/acs.accounts.6b00068
158. Balcells D, Clot E, Eisenstein O et al (2016) Deciphering selectivity in organic reactions: a
multifaceted problem. Acc Chem Res 49:1070–1078. https://doi.org/10.1021/acs.accounts.
6b00099
302
M. Reid
halides employing a two-chamber reactor: a protocol for the synthesis of aryl aldehydes
including 13 C- and D-isotope labeling. J Org Chem 78:6112–6120. https://doi.org/10.1021/
jo400741t
145. Boga SB, Alhassan AB, Hesk D (2014) Efficient synthesis of
2
H &
13
C labeled benzaldehydes
via regio-selective formylation. Tetrahedron Lett 55:4442–4444. https://doi.org/10.1016/j.
tetlet.2014.06.053
146. Kerr WJ, Reid M, Tuttle T (2017) Iridium-catalyzed formyl-selective deuteration of aldehydes. Angew Chem Int Ed 56:7808–7812. https://doi.org/10.1002/anie.201702997
147. Fortman GC, Jacobsen H, Cavallo L, Nolan SP (2011) Catalytic deuteration of silanes
mediated by N-heterocyclic carbene-Ir(III) complexes. Chem Commun 47:9723. https://doi.
org/10.1039/c1cc13492b
148. Iluc VM, Fedorov A, Grubbs RH (2012) H/D exchange processes catalyzed by an iridiumpincer complex. Organometallics 31:39–41. https://doi.org/10.1021/om201049p
149. Nelson DJ, Egbert JD, Nolan SP (2013) Deuteration of boranes: catalysed versus
non-catalysed processes. Dalton Trans 42:4105. https://doi.org/10.1039/c3dt33045a
150. Garnett JL, Hodges RJ (1967) Homogeneous metal-catalyzed exchange of aromatic compounds. Isotopic hydrogen labeling procedure. J Am Chem Soc 89:4546–4547. https://doi.org/
10.1021/ja00993a067
151. Lockley WJS (1982) Regioselective deuteration of aromatic and α,β-unsaturated carboxylic
acids via rhodium(III) chloride catalysed exchange with deuterium oxide. Tetrahedron Lett
23:3819–3822. https://doi.org/10.1016/S0040-4039(00)87716-3
152. Anderson GK, Saum SE, Cross RJ, Morris SA (1983) Homogeneous catalysts of hydrogendeuterium exchange reactions involving cyclopentadienyl complexes of palladium and platinum. Organometallics 2:780–782. https://doi.org/10.1021/om00078a021
153. Heys R (1992) Investigation of [IrH 2 (Me 2 CO) 2 (PPh 3 ) 2 ]BF 4 as a catalyst of hydrogen isotope
exchange of substrates in solution. J Chem Soc Chem Commun 680. https://doi.org/10.1039/
c39920000680
154. Maldonado AG, Rothenberg G (2010) Predictive modeling in homogeneous catalysis: a
tutorial. Chem Soc Rev 39:1891–1902. https://doi.org/10.1039/b921393g
155. Houk KN, Cheong PH-Y (2008) Computational prediction of small-molecule catalysts. Nature
455:309–313. https://doi.org/10.1038/nature07368
156. Peng Q, Duarte F, Paton RS (2016) Computing organic stereoselectivity – from concepts to
quantitative calculations and predictions. Chem Soc Rev 45:6093–6107. https://doi.org/10.
1039/c6cs00573j
157. Sperger T, Sanhueza IA, Schoenebeck F (2016) Computation and experiment: a powerful
combination to understand and predict reactivities. Acc Chem Res 49:1311–1319. https://doi.
org/10.1021/acs.accounts.6b00068
158. Balcells D, Clot E, Eisenstein O et al (2016) Deciphering selectivity in organic reactions: a
multifaceted problem. Acc Chem Res 49:1070–1078. https://doi.org/10.1021/acs.accounts.
6b00099
302
M. Reid