10.1002/anie.201706893
Angewandte Chemie International Edition
COMMUNICATION
1413–1426; d) F. Röhrig, A. Schulze, Nat. Rev. Cancer 2016, 16, 732–
749.
[4]
[5]
For reviews on carbonyl dehydrogenation, see: a) D. Walker, J. D.
Hiebert, Chem. Rev. 1967, 67, 153–195; b) H. J. Reich, S. Wollowitz,
Org. React. 1993, 44, 1–200; c) J. Muzart, Eur. J. Org. Chem. 2010,
3779–3790; d) S. S. Stahl, T. Diao, Comp. Org. Synth. 2014, 7, 178–
212; e) A. Turlik, Y. Chen, T. R. Newhouse, Synlett 2016, 27, 331–336.
f) A. V. Iosub, S. S. Stahl, ACS Catal. 2016, 6, 8201–8213.
For ester dehydrogenation involving a-phenylselenide, see: H. J.
Reich, I. L. Reich, J. M. Renga, J. Am. Chem. Soc. 1973, 95, 5813–
5815; b) K. B. Sharpless, R. F. Lauer, A. Y. Teranishi, J. Am. Chem.
Soc. 1973, 95, 6137–6139.
[6]
[7]
For ester dehydrogenation via dehydrosulfenylation, see: B. M. Trost,
T. N. Salzmann, K. Hirio, J. Am. Chem. Soc. 1976, 98, 4887–4902.
For
a comparison of a-halogenation and elimination to other
dehydrogenation methods, see: J. A. Marco, M. Carda, Tetrahedron
1978, 43, 2523–2532.
[8]
a) S. J. D. Mari, R. N. Brady, E. E. Snell, Archives of Biochemistry and
Biophysics 1971, 143, 553–565; b) M. Nakano, Y. Fujino, Agr. Biol.
Chem. 1975, 39, 707–710; c) N. Kallscheuer, T. Polen, M. Bott, J.
Marienhagen, Metabolic Engineering 2017, 42, 33–42.
[9]
G. Cainelli, G. Cardillo, A. U. Ronchi, J. C. S. Chem. Comm. 1973, 94–
95.
[10]
a) Y. Chen, J. P. Romaire, T. R. Newhouse, J. Am. Chem. Soc. 2015,
137, 5875–5878; b) Y. Chen, A. Turlik, T. R. Newhouse, J. Am. Chem.
Soc. 2016, 138, 1166–1169; c) Y. Chen, D. Huang, Y. Zhao, T. R.
Newhouse, Angew. Chem. Int. Ed. 2017, 56, 8258–8262.
For the limited number of examples of X-ray structures of C-bound
palladium enolates of carboxylic acids, see: a) Y. Zenitani, K. Inoue, Y.
Kai, N. Yasuoka, N. Kasai, Bull. Chem. Soc. Jpn. 1976, 49, 1531–
1537; b) A. K. Bar, R. Chakrabarty, P. S. Mukherjee, Organometallics
2008, 27, 3806–3810; c) I. A. Efimenko, L. I. Demina, P. V.
Ankudinova, A. V. Churakov, N. A. Ivanova, O. S. Erofeeva, Russ. J.
Inorg. Chem. 2016, 61, 1252–1256.
[11]
[12]
[13]
[14]
For a seminal example of palladium-catalyzed decarboxylation of
aliphatic acids to synthesize a-olefins, see: T. A. Foglia, P. A. Barr, J.
Am. Oil Chem. Soc. 1976, 53, 737–741.
For a review on transition-metal catalyzed decarboxylation, including
with palladium, see: N. Rodríguez, L. J. Goossen, Chem. Soc. Rev.
2011, 40, 5030–5048.
For carboxylic acid a-alkylation via enediolates, see: a) P. L. Creger, J.
Am. Chem. Soc. 1967, 89, 2500–2501; b) P. E. Pfeffer, L. S. Silbert, J.
M. Chirinko, J. Org. Chem. 1972, 37, 451–458; c) A. Streitwieser, M.
Husemann, Y.-J. Kim, J. Org. Chem. 2003, 68, 7937–7942.
For reviews on enediolates used in synthetic chemistry, see: a) C. M.
Thompson, D. L. C. Green, Tetrahedron 1991, 47, 4223–4285; b) S.
Gil, M. Parra, Curr. Org. Chem. 2002, 6, 283–302.
[15]
[16]
[17]
For a lead reference on multi-metallic amido zinc complexes, see: Y.-
H. Chen, M. Ellwart, G. Toupalas, Y. Ebe, P. Knochel, Angew. Chem.
Int. Ed. 2017, 56, 4612–4616.
Similar outcomes observed with Zn(OTf)2 in place of ZnCl2 (1H-NMR
yield of 90%) suggest the yield enhancement does not depend on
chloride. Greater than 6.0 equiv ZnCl2 had minimal impact on reaction
efficiency.
[18]
[19]
A. C. Biessember, A. Levina, G. C. Fu, J. Am. Chem. Soc. 2012, 134,
14232–14237.
a) F. Pan, Z.-Q. Lei, H. Wang, H. Li, J. Sun, Z.-J. Shi, Angew. Chem.
Int. Ed. 2013, 52, 2063–2067; b) R. Qiu, L. Zhang, C. Xu, Y. Pan, H.
Pang, L. Xu, H. Li, Adv. Synth. Catal. 2015, 357, 1229–1236.
For a review on decarboxylative functionalization of cinnamic acids,
see: A. J. Borah, G. Yan, Org. Biomol. Chem. 2015, 13, 8094–8115.
M. Yamashita, K. Hirano, T. Satoh, M. Miura, Org. Lett. 2010, 12, 592–
595.
K. Meraz, K. K. Gnanasekaran, R. Thing, R. A. Bunce, Tetrahedron
Lett. 2016, 57, 5057–5061.
G. K. S. Prakash, P. Yan, B. Török, G. A. Olah, Catalysis Lett. 2003,
87, 109–112.
[20]
[21]
[22]
[23]
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