Organic Letters
Letter
Oxidative Cyclization. Org. Lett. 2017, 19, 1706−1709. (d) Mei, S.-T.;
Wang, N.-J.; Ouyang, Q.; Wei, Y. Rhodium-catalysed direct C−H
allylation of N-sulfonyl ketimines with allyl carbonates. Chem.
Commun. 2015, 51, 2980−2983.
Chem. 1991, 56, 6034−6038. (f) Fodor, G.; Nagubandi, S.
Correlation of the von Braun, Ritter, Bischler-Napieralski, Beckmann
and Schmidt reactions via nitrilium salt intermediates. Tetrahedron
1980, 36, 1279−1300. (g) Vaccari, D.; Davoli, P.; Ori, C.; Spaggiari,
A.; Prati, F. A Very Mild Access to 3,4-Dihydroisoquinolines Using
Triphenyl Phosphite-Bromine-Mediated Bischler-Napieralski-Type
Cyclization. Synlett 2008, 2008, 2807−2810.
(10) (a) Manan, R. S.; Zhao, P. Merging rhodium-catalysed C−H
activation and hydroamination in a highly selective [4 + 2] imine/
alkyne annulation. Nat. Commun. 2016, 7, 11506−11517. (b) Jia, T.;
Zhao, C.; He, R.; Chen, H.; Wang, C. Iron-Carbonyl-Catalyzed
Redox-Neutral [4 + 2] Annulation of N−H Imines and Internal
Alkynes by C−H Bond Activation. Angew. Chem., Int. Ed. 2016, 55,
5268−5271. (c) He, K.-H.; Zhang, W.-D.; Yang, M.-Y.; Tang, K.-L.;
Qu, M.; Ding, Y.-S.; Li, Y. Redox-Divergent Hydrogen-Retentive or
Hydrogen-Releasing Synthesis of 3,4-Dihydroisoquinolines or Iso-
quinolines. Org. Lett. 2016, 18, 2840−2843.
(11) For selected papers and review, see: (a) Cochran, B. M.;
Michael, F. E. Synthesis of 2,6-Disubstituted Piperazines by a
Diastereoselective Palladium-Catalyzed Hydroamination Reaction.
Org. Lett. 2008, 10, 329−332. (b) Liu, X.-Y.; Li, C.-H.; Che, C.-M.
Phosphine Gold(I)-Catalyzed Hydroamination of Alkenes under
Thermal and Microwave-Assisted Conditions. Org. Lett. 2006, 8,
2707−2710. (c) McGhee, A.; Cochran, B. M.; Stenmark, T. A.;
Michael, F. E. Stereoselective synthesis of 2,5-disubstituted morpho-
lines using a palladium-catalyzed hydroamination reaction. Chem.
Commun. 2013, 49, 6800−6802. (d) Huang, L.; Arndt, M.; Gooβen,
K.; Heydt, H.; Gooβen, L. J. Late Transition Metal-Catalyzed
Hydroamination and Hydroamidation. Chem. Rev. 2015, 115, 2596−
2697.
(4) For selected papers, see: (a) Trita, A. S.; Biafora, A.; Pichette
Drapeau, M.; Weber, P.; Gooβen, L. J. Regiospecific ortho-C−H
Allylation of Benzoic Acids. Angew. Chem., Int. Ed. 2018, 57, 14580−
14584. (b) Kumar, G. S.; Kapur, M. Ruthenium-Catalyzed, Site-
Selective C−H Allylation of Indoles with Allyl Alcohols as Coupling
Partners. Org. Lett. 2016, 18, 1112−1115. (c) Kim, M.; Sharma, S.;
Mishra, N. K.; Han, S.; Park, J.; Kim, M.; Shin, Y.; Kwak, J. H.; Han,
S. H.; Kim, I. S. Direct allylation of aromatic and α,β-unsaturated
carboxamides under ruthenium catalysis. Chem. Commun. 2014, 50,
11303−11306. (d) Oi, S.; Tanaka, Y.; Inoue, Y. Ortho-Selective
Allylation of 2-Pyridylarenes with Allyl Acetates Catalyzed by
Ruthenium Complexes. Organometallics 2006, 25, 4773−4778.
́
́
(5) For selected papers, see: (a) Gensch, T.; Vasquez-Cespedes, S.;
Yu, D.-G.; Glorius, F. Cobalt(III)-Catalyzed Directed C−H
Allylation. Org. Lett. 2015, 17, 3714−3717. (b) Suzuki, Y.; Sun, B.;
Sakata, K.; Yoshino, T.; Matsunaga, S.; Kanai, M. Dehydrative Direct
C-H Allylation with Allylic Alcohols under [Cp*CoIII] Catalysis.
Angew. Chem., Int. Ed. 2015, 54, 9944−9947. (c) Lorion, M. M.;
Kaplaneris, N.; Son, J.; Kuniyil, R.; Ackermann, L. Late-Stage Peptide
Diversification through Cobalt-Catalyzed C−H Activation: Sequential
Multicatalysis for Stapled Peptides. Angew. Chem., Int. Ed. 2019, 58,
1684−1688.
(6) (a) Liu, W.; Richter, S. C.; Zhang, Y.; Ackermann, L.
Manganese(I)-Catalyzed Substitutive C−H Allylation. Angew.
Chem., Int. Ed. 2016, 55, 7747−7750.
(7) (a) Wang, H.; Lorion, M. M.; Ackermann, L. Domino C−H/N−
H Allylations of Imidates by Cobalt Catalysis. ACS Catal. 2017, 7,
3430−3433. (b) Bairy, G.; Das, S.; Begam, H. M.; Jana, R.
Exceedingly Fast, Direct Access to Dihydroisoquinolino[1,2-b]-
quinazolinones through a Ruthenium(II)-Catalyzed Redox-Neutral
C−H Allylation/Hydroamination Cascade. Org. Lett. 2018, 20,
7107−7112. (c) Xia, Y.-Q.; Dong, L. Ruthenium(II)-Catalyzed
Indolo[2,1-a]isoquinolines Synthesis by Tandem C−H Allylation
and Oxidative Cyclization of 2-Phenylindoles with Allyl Carbonates.
Org. Lett. 2017, 19, 2258−2261. (d) Manna, M. K.; Bairy, G.; Jana, R.
Sterically Controlled Ru(II)-Catalyzed Divergent Synthesis of 2-
Methylindoles and Indolines through a C−H Allylation/Cyclization
Cascade. J. Org. Chem. 2018, 83, 8390−8400. (e) Zeng, R.; Fu, C.;
Ma, S. Highly Selective Mild Stepwise Allylation of N-Methox-
ybenzamides with Allenes. J. Am. Chem. Soc. 2012, 134, 9597−9600.
(8) For selected papers and review, see: (a) Christopher, J. A.;
Atkinson, F. L.; Bax, B. D.; Brown, M. J. B.; Champigny, A. C.;
Chuang, T. T.; Jones, E. J.; Mosley, J. E.; Musgrave, J. R. 1-Aryl-3,4-
dihydroisoquinoline inhibitors of JNK3. Bioorg. Med. Chem. Lett.
2009, 19, 2230−2234. (b) Bentley, K. W. β-Phenylethylamines and
the isoquinoline alkaloids. Nat. Prod. Rep. 2001, 18, 148−170.
(c) Michael, J. P. Quinoline, quinazoline and acridone alkaloids. Nat.
Prod. Rep. 2002, 19, 742−760. (d) Scott, J. D.; Williams, R. M.
Chemistry and Biology of the Tetrahydroisoquinoline Antitumor
Antibiotics. Chem. Rev. 2002, 102, 1669−1730.
(12) For selected papers of benzodioxoles, see: (a) Xu, Y.-Z.; Yuan,
S.; Bowers, S.; Hom, R. K.; Chan, W.; Sham, H. L.; Zhu, Y. L.; Beroza,
P.; Pan, H.; Brecht, E.; Yao, N.; Lougheed, J.; Yan, J.; Tam, D.; Ren,
Z.; Ruslim, L.; Bova, M. P.; Artis, D. R. Design and synthesis of
thiophene dihydroisoquinolines as novel BACE1 inhibitors. Bioorg.
Med. Chem. Lett. 2013, 23, 3075−3080. For selected papers of
thiophenes, see: (b) Ghorab, M. M.; Alsaid, M. S.; Al-Dosari, M. S.;
Ragab, F. A.; Al-Mishari, A.; Almoqbil, A. N. Novel quinolines
carrying pyridine, thienopyridine, isoquinoline, thiazolidine, thiazole
and thiophene moieties as potential anticancer agents. Acta Pharm.
2016, 66, 155−171. (c) Yu, S.; Oh, J.; Li, F.; Kwon, Y.; Cho, H.; Shin,
J.; Lee, S. K.; Kim, S. New Scaffold for Angiogenesis Inhibitors
Discovered by Targeted Chemical Transformations of Wondonin
Natural Products. ACS Med. Chem. Lett. 2017, 8, 1066−1071.
(13) (a) Hanley, P. S.; Hartwig, J. F. Migratory Insertion of Alkenes
into Metal−Oxygen and Metal−Nitrogen Bonds. Angew. Chem., Int.
Ed. 2013, 52, 8510−8525. (b) Chirik, P. J.; Bercaw, J. E.
Cyclopentadienyl and Olefin Substituent Effects on Insertion and β-
Hydrogen Elimination with Group 4 Metallocenes. Kinetics,
Mechanism, and Thermodynamics for Zirconocene and Hafnocene
Alkyl Hydride Derivatives. Organometallics 2005, 24, 5407−5423.
(c) Zhao, D.; Lied, F.; Glorius, F. Rh(III)-catalyzed C−H
functionalization/aromatization cascade with 1,3-dienes: a redox-
neutral and regioselective access to isoquinolines. Chem. Sci. 2014, 5,
2869−2873. (d) Azpeitia, S.; Prieto, U.; San Sebastian, E.; Rodriguez-
Dieguez, A.; Garralda, M. A.; Huertos, M. A. Alkene-alkyl
interconversion: an experimental and computational study of the
olefin insertion and β-hydride elimination processes. Dalton Trans
2018, 47, 6808−6818.
(9) For selected papers, see: (a) Hu, X.; Zhang, G.; Bu, F.; Lei, A.
Selective Oxidative [4 + 2] Imine/Alkene Annulation with H2
Liberation Induced by Photo-Oxidation. Angew. Chem., Int. Ed.
2018, 57, 1286−1290. (b) Riemer, D.; Schilling, W.; Goetz, A.;
́
Zhang, Y.; Gehrke, S.; Tkach, I.; Holloczki, O.; Das, S. CO2-Catalyzed
(14) Haibach, M. C.; Seidel, D. C−H Bond Functionalization
through Intramolecular Hydride Transfer. Angew. Chem., Int. Ed.
2014, 53, 5010−5036.
Efficient Dehydrogenation of Amines with Detailed Mechanistic and
Kinetic Studies. ACS Catal. 2018, 8, 11679−11687. (c) Movassaghi,
M.; Hill, M. D. A Versatile Cyclodehydration Reaction for the
Synthesis of Isoquinoline and β-Carboline Derivatives. Org. Lett.
2008, 10, 3485−3488. (d) Awuah, E.; Capretta, A. Strategies and
Synthetic Methods Directed Toward the Preparation of Libraries of
Substituted Isoquinolines. J. Org. Chem. 2010, 75, 5627−5634.
(e) Larsen, R. D.; Reamer, R. A.; Corley, E. G.; Davis, P.; Grabowski,
E. J. J.; Reider, P. J.; Shinkai, I. A modified Bischler-Napieralski
procedure for the synthesis of 3-aryl-3,4-dihydroisoquinolines. J. Org.
E
Org. Lett. XXXX, XXX, XXX−XXX