10.1002/chem.201700587
Chemistry - A European Journal
ICATION
Campo, Angew. Chem. Int. Ed. 20013, 52, 9896-9898; d) G. Rouquet, N.
Chatani, Angew. Chem. Int. Ed. 20013, 52, 11726-11743.
ERC Grant Agreement No. 307535) is gratefully
[8]
[9]
a) G. Cera, T. Haven, L. Ackermmann Angew. Chem. Int. Ed. 2016, 55,
1484-1488; b) K. Graczyk, T. HHaven, L. Ackermann Chem. Eur. J.
2015, 21, 8812-8815; c) Q. Qu, HH. H. Al Mamari, K. Graczyk, E. Diers,
L. Ackermann, Angew. Chem. Int.. Ed. 2014, 53, 3868-3871.
H activation • alkynes• heterocycles •iron •
For reviews on iron catalysis: a) G. Cera, L. Ackermann, Top. Curr.
Chem. 2016, DOI: 10.1007/s410661-016-0059-6; b) O. M. Kuzmina, A. K.
Steib, A. Moyeux, G. Cahiez, P. Knochel, Synthesis 2015, 47, 1696-
1705; c) A. Fürstner, Angew. Chhem. Int. Ed. 2014, 53, 8587-8598; d)
C.–L. Sun, B.–J. Lie, Z.–J. Shi, CChem. Rev. 2011, 111, 1293−1314; e)
S. Enthaler, K. Junge, M. Beller, Angew. Chem. Int. Ed. 2008, 47,
3317−3321; f) Iron Catalysis in Organic Chemistry B. Plietker, Ed.;
Wiley-VCH: Weinheim, 2008; g) A. Correa, O. Garcia Mancheño, C.
Bolm, Chem. Soc. Rev. 2008, 377, 1108-117; h) C. Bolm, J. Legros, J.
Le Paih, L. Zani, Chem. Rev. 20044, 104, 6217−6254.
illa, C. Najera, Chem. Rev. 2014, 114, 1783-1826; b) I. C.
Gold, J. Org. Chem. 2013, 78, 7777-7784; c) A. Palisse, S.
rg. Biomol. Chem. 2012, 10, 8041-8047; d) J. Liu, J. W. Y.
Tang, Chem. Rev. 2009, 109, 5799-5867; e) F. Kivala, M.
cc. Chem. Res. 2009, 42, 235-248.
, P. J. Stang in Acetylene Chemistry: Chemistry, Biology
Science, Wiley-VCH, Weinheim, 2005.
see: a) J. Waser, Top. Curr. Chem. 2015, 373, 187-222; b)
J. Waser, Chem. Soc. Rev. 2012, 41, 4165−4179; c) A. S.
Gevorgyan, Angew. Chem. Int. Ed. 2010, 49, 2096−2098; d)
Correa, C. Bolm, Angew. Chem. Int. Ed. 2008, 120, 4940-
–i. Negishi, L. Anastasia, Chem. Rev. 2003, 103, 1979-
Sonogashira, J. Organomet. Chem. 2002, 653, 46-49; g) H.
. Hierso, Angew. Chem. Int. Ed. 2007, 46, 834-871; h) C.
Echavarren, Synthesis 2005, 2, 167-182.
[10] For recent progress on iron-catalyyzed C–H functionalizations see: a) R.
Shang, L. Ilies, E. Nakamura, J. Am. Chem. Soc. 2016, 138, 10132-
10135; b) T. Matsubara, L. Ilies, EE. Nakamura, Chem. Asian J. 2016, 11,
380-384; c) T. Jia, C. Zhao, R. HHe, H. Chen, C. Wang, Angew. Chem.
Int. Ed. 2016, 55, 5268-5271; d) II.T. Alt, B. Plietker, Angew. Chem. Int.
Ed. 2016, 55, 1519-1522; e) R. SShang, L. Ilies, E. Nakamura, J. Am.
Chem. Soc. 2015, 137, 7663−76660; f) M. Y. Wong, T. Yamakawa, N.
Yoshikai, Org. Lett. 2015, 17, 4422-445; g) R. Shang, L. Ilies, S. Asako,
E. Nakamura, J. Am. Chem. Soc.. 2014, 136, 14349−14352; h) L. Ilies,
T. Matsubara, S. Ichikawa, S. Asaako, E. Nakamura, J. Am. Chem. Soc.
2014, 136, 13126−13129; i) E. R. Fruchey, B. M. Monks, S. P. Cook, J.
Am. Chem. Soc. 2014, 136, 133130−13133; j) B. M. Monks, E. R.
Fruchey, S. P. Cook, Angew. Cheem. Int. Ed. 2014, 53, 11065-11069; k)
S. Asako, J. Norinder, L. Ilies, N. Yoshikai, E. Nakamura, Adv. Synth.
Catal. 2014, 356, 1481−1485; l) SS. Asako, L. Ilies, E. Nakamura, J. Am.
Chem. Soc. 2013, 135, 177555−1775; m) R. Shang, L. Ilies, A.
Matsumoto, E. Nakamura, J. Am. Chem. Soc. 2013, 135, 6032−6030.
[11] K. S. Egorova, V. P. Ananikov, Anngew. Chem. Int. Ed. 2016, 55, 12150-
12162 and references cited thereiin.
ve recent reviews on C−H activation: a) T. Gensch, M. N.
F. Glorius, J. Wencel-Delord, Chem. Soc. Rev. 2016, 45,
b) C. Borie, L. Ackermann, M. Nechab, Chem. Soc. Rev.
68−1386; c) J.–K. Kim, K. Shin, S. Chang, Top. Organomet.
, 55, 29−51; d) S.–A. Girard, T. Knauber, C –J. Li, Angew.
Ed. 2014, 53, 74−100; e) G. Rouquet, N. Chatani, Angew.
Ed. 2013, 52, 11726−11743; f) P. B. Arockiam, C. Bruneau,
uf, Chem. Rev. 2012, 112, 5879−5918; g) T. Satoh, M.
m. Eur. J. 2010, 16, 11212−11222; h) R. Giri, B.–F. Shi, K.–
Maugel, J.–Q. Yu, Chem. Soc. Rev. 2009, 3, 3242−3272;
ann, R. Vicente, A. Kapdi, Angew. Chem. Int. Ed. 2009, 48,
j) R. G. Bergman, Nature 2007, 446, 391−393 and
ited therein.
[12] L. Ackermann, Acc. Chem. Res. 22014, 47, 281-295.
examples of 4d or 5d metal-catalyzed C–H alkynylations,
e, C. Xu, L. Wojtas, N. G. Akhmedov, H. Chen, X. Shi, Org.
18, 2970-2973; b) R. Boobalan, P. Gandeepan, C.-H.
Lett. 2016, 18, 3314-3317; c) F. Xie, Z. Qi, S. Yu, X. Li, J.
Soc. 2014, 136, 4780-4787; d) C. Feng, T.-P. Loh, Angew.
Ed. 2014, 53, 2722-2726; e) Y. Ano, M. Tobisu, N. Chatani,
2, 23, 2763-2767; f) S. H. Kim, S. H. Park, S. Chang,
, 2012, 68, 5162-5166; g) L. Ackermann, C. Kornhaaß, Y.
ett. 2012, 14, 1824-1826; h) T. de Haro, C. Nevado, J. Am.
2010, 132, 1512-1513; i) J. P. Brand, J. Charpentier, J.
ew. Chem. Int. Ed. 2009, 48, 9346-9349; j) M. Tobisu, Y.
atani, Org. Lett. 2009, 11, 3250-3252; k) I. V. Seregin, V.
Gevorgyan, J. Am. Chem. Soc. 2007, 129, 7742-7743.
see: a) V. G. Landge, C. H. Shewale, G. Jaiswal, M. K.
. Midya, E. Balaraman, Catal. Sci. Technol. 2016, 6, 1946-
Ruan, S. Lackner, L. Ackermann, ACS Catal. 2016, 6,
c) J. Yi, L. Yang, C. Xia, F. Li, J. Org. Chem. 2015, 80,
d) Y.-H. Liu, Y.-J. Liu, S.-Y. Yan, B.-F. Shi, Chem. Commun.
1650-11653; e) Y.-H. Liu, Y.-J. Liu, S.-Y. Yan, B.-F. Shi,
mun. 2015, 51, 6388-6391. For copper, see: f) Y.-J. Liu, Y.-
Yin, W.-J. Gu, B.-F. Shi, Chem. Eur. J. 2015, 21, 205-209;
, H.-L. Wang, S.-Z. Sun, H.-X. Dai, J.-Q. Yu, J. Am. Chem.
136, 11590-11593. For cobalt, see: h) V. G. Landge, G.
Balaraman, Org. Lett. 2016, 18, 812-815; i) J. Zhang, H.
, Z. Liu, C. Wang, Y. Zhang, J. Am. Chem. Soc. 2015, 137,
6; j) N. Sauermann, M. J. Gonzàlez, L. Ackermann, Org.
7, 5316-5319; k) Z.-Z. Zhang, B. Liu, C.-Y. Wang, B.-F. Shi,
15, 17, 4094-4097.
[13] For examples of triazolyl-amine (TTAM) assisted C–H functionalizations
see: a) D. Santrac, S. Cella, W. Wang, L. Ackermann, Eur. J. Org.
Chem. 2016, 5429-5436; b) XX. Ye, Y. Zhang, Y. He, X. Shi,
Tetrahedron 2016, 72, 2756-27622; c) G. Zhang, X. Xie, J. Zhu, S. Li, C.
Ding, D. Ding, Org. Biomol. Cheem. 2015, 13, 5444–5450 d) H. H. Al
Mamari, E. Diers, L. Ackermann, Chem. -Eur. J. 2014, 20, 9739-9743.
For examples of 1,2,3 triazole-asssisted C–H functionalizations see: e) A.
Irastorza, J. M. Aizpurua, A. Corrrea, Org. Lett. 2016, 18, 1080-1083; f)
X. Ye, X. Shi, Org. Lett. 2014, 16, 4448-4451; g) X. Ye, Z. He, T.
Ahmed, X. Shi, Chem. Sci. 20133, 4, 3712-3716; h) L. Ackermann, R.
Born, R. Vicente, Chem. Sus. Cheem. 2009, 2, 546-549; i) L. Ackermann,
H. K. Potukuchi, D. Landsberg, RR. Vicente, Org. Lett. 2008, 10, 3081-
3084.
[14] For detailed information, see the SSupporting Information.
[15] For a review on Bischler-Napierallski and Pictet-Spengler reactions, see
a review: V. A. Glushkov, Y. V. SShklyaev, Chem. Heterocycl. Compd.
2001, 37, 663-687.
[16] For representative examples oof isoquinolone synthesis via C–H
functionalizations, see: a) X.-Q Hao, C. Du, X. Zhu, P.-X. Li, J.-H.
Zhang, J.-L. Niu, M.-P. Song, OOrg. Lett. 2016, 18, 3610-3613; b) G.
Sivakumar, A. Vijeta, M. Jeganmoohan, Chem. -Eur. J. 2016, 22, 5899-
5903; c) N. J. Webb, S. P. Maddsen, S. A. Raw, Org. Lett. 2014, 16,
4716-4721; d) H. Wang, C. Grohmmann, C. Nimphius, F. Glorius, J. Am.
Chem. Soc. 2012, 134, 19592-199595; e) L. Ackermann, A. V. Lygin, N.
Hoffmann, Angew. Chem. Int. Ed. 2011, 123, 6503-6506; f) H. Shiota, Y.
Ano, Y. Aihara, Y. Fukumoto, N. CChatani, J. Am. Chem. Soc. 2011, 133,
14952-14955; g) B. Li, H. Feng, SS. Xu, B. Wang, Chem. Eur. J. 2011,
17, 12573-12577; h) L. Ackermaann, S. Fenner, Org. Lett. 2011, 13,
6548-6551; i) T. K. Hyster, T. RRovis, J. Am. Chem. Soc. 2010, 132,
reviews, see: a) R. K. Rit, M. R. Yadav, K. Ghosh, A. K.
ahedron 2015, 71, 4450-4459; b) O. Daugulis, J. Roane, L.
c. Chem. Res. 2015, 48, 1053-1064; c) M. Corbet, F. De
This article is protected by copyright. All rights reserved.