Journal of the American Chemical Society
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R. Frankenstein, and S. Burkhardt for NMR
g) Modern Allene Chemistry. Krause, N. and Hashmi,
A.S.K., Eds. VCH: Weinheim, 2004; Vols. 1 and 2; h) Ma,
S. Top. Organomet. Chem. 2005, 14, 183-210.
[12] For reviews on the synthesis and utility of allenes, see:
a) Ma, S. Chem. Rev. 2005, 105, 2829-2872; b) Yu, S.; Ma,
S. Angew. Chem. Int. Ed. 2012, 51, 3074-3112.
measurements. Tobias Schnitzer and Patrick Hilpert (ETH
Zürich) are acknowledged for their assistance with SFC
analysis, and Prof. Helma Wennemers (ETH Zürich) is
thanked for SFC access.
[13] For examples employing Ir and Ru, see: a) Skucas, E.;
Bower, J.F.; Krische, M.K. J. Am. Chem. Soc. 2007, 129,
12678-12679; b) Han, S.B.; Kim, I.S.; Han, H.; Krische,
M.J. J. Am. Chem. Soc. 2009, 131, 6916-6917; c) Moran,
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2011, 3, 287-290; d) Ngai, M.-Y.; Skucas, E.; Krische,
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T.P.; Krische, M.J. Org. Lett. 2013, 15, 3790-3793; g)
Park, B.Y.; Nguyen, K.D.; Chaulagain, M.R.; Komanduri,
V.; Krische, M.J. J. Am. Chem. Soc. 2014, 136, 11902-
11905; h) Liang, T.; Nguyen, K.D.; Zhang, W.; Krische,
M.J. J. Am. Chem. Soc. 2015, 137, 3161-3164; i) Sam, B.;
Luong, T.; Krische, M.J. Angew. Chem. Int. Ed. 2015, 54,
5465-5469; j) Oad, S.; Sam, B.; Krische, M.J. Angew.
Chem. Int. Ed. 2015, 54, 8525-8528.
[14] For examples using Cu, see: a) For reviews, see: a)
Shimizu, Y.; Kanai, M. Tetrahedron Lett. 2014, 55, 3727-
3737; b) Pulis, A.P.; Yeung, K.; Proctor, D.J. Chem. Sci.
2017, 8, 5240-5247; c) Jung, B.; Hoveyda, A.H. J. Am.
Chem. Soc. 2012, 134, 1490-1493; d) Yuan, W.; Ma, S.
Adv. Synth. Catal. 2012, 354, 1867-1872; e) Meng, F.;
Jung, B.; Haeffner, F.; Hoveyda, A.H. Org. Lett. 2013, 15,
1414-1417; f) Semba, K.; Shinomiya, M.; Fujihara, T.;
Terao, J.; Tsui, Y, Chem. Eur. J. 2013, 19, 7125-7132; g)
Meng, F.; Jang, H.; Hung, B.; Hoveyda, A.H. Angew.
Chem. Int. Ed. 2013, 52, 5046-5051; h) Jang, H.; Jung, B.;
Hoveyda, A.H. Org. Lett. 2014, 16, 4658-4661; i) Yani,
Y.; Fujihara, T.; Terao, J.; Tsuji, Y. J. Am. Chem. Soc.
2014, 136, 17706-17709; j) Zhou, Y.; You, W.; Smith,
K.B, Brown, M.K. Angew. Chem. Int. Ed. 2014, 53, 3475-
3479; k) Zhao, W.; Montgomery, J. J. Am. Chem. Soc.
2016, 138, 9763-9766.
[15] For examples using Rh, see: a) Wolf, J.; Werner, H.
Organometallics 1987, 6, 1164-1169; b) Koschker, P.;
Breit, B. Acc. Chem. Res. 2016, 49, 1524-1536; c)
Lumbroso, A.; Koschker, P.; Vautravers, N.R.; Breit, B. J.
Am. Chem. Soc. 2011, 133, 2386-2389; d) Koschker, P.;
Lumbroso, A.; Breit, B. J. Am. Chem. Soc. 2011, 133,
20746-20749; e) Gellrich, U.; Meißner, A.; Steffani, A.;
Kähny, M.; Drexler, H.-J.; Heller, D.; Plattner, D.A.; Breit,
B. J. Am. Chem. Soc. 2014, 136, 1097-1104; f) Xu, K.;
Thieme, N.; Breit, B. Angew. Chem. Int. Ed. 2014, 53,
2162-2165; g) Xu, K.; Khakyzadeh, V.; Bury, T.; Breit, B.
J. Am. Chem. Soc. 2014, 136, 16124-16127; h) Pritzius,
A.B.; Breit, B.; Angew. Chem. Int. Ed. 2015, 54, 3121-
3125; i) Haydl, A.M.; Xu, K.; Breit, B. Angew. Chem. Int.
Ed. 2015, 54, 7149-7153; j) Xu, K.; Gilles, T.; Breit, B.
Nat. Commun. 2015, 6, 1-7; k) Pritzius, A.B.; Breit, B.
Angew. Chem. Int. Ed. 2015, 54, 15818-15822; l) Spreider,
PA.; Haydl, A.M.; Heinrich, M.; Breit, B. Angew. Chem.
Int. Ed. 2016, 55, 15569-15573; m) Thieme, N.; Breit, B.
Angew. Chem. Int. Ed. 2017, 56, 1520-1524; n) Cruz, F.;
Dong, V.M. J. Am. Chem. Soc. 2017, 139, 1029-1032; o)
Cruz, F.; Zhu, Y.; Tercenio, Q.D.; Shen, Z.; Dong, V.M.
J. Am. Chem. Soc. 2017, 139, 10641-10644; p) Chen. Z;
Dong, V.M. Nat. Commun. 2017, 8, 784; q) Haydl, A.M.;
Berthold, D.; Spreider, P.A.; Breit, B. Angew. Chem. Int.
Ed. 2016, 55, 5765-5769; r) Haydl, A.M.; Breit, B. Chem.
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