First author et al.
Report
2016, 138, 5515−5518; (g) Zeng, X.; Liu, S.; Shi, Z.; Liu, G.; Xu, B.
Zhu, X.-Q.; Shang, M.; Ye, L.-W. Reversal of Regioselectivity in
Ynamide Chemistry. ACS Catal. 2019, 9, 6393−6406; (b) Pan, F.; Shu,
C.; Ye, L.-W. Recent progress towards gold-catalyzed synthesis of
N-containing tricyclic compounds based on ynamides. Org. Biomol.
Chem. 2016, 14, 9456−9465; (c) Evano, G.; Theunissen, C.; Lecomte,
M. Ynamides: Powerful and Versatile Reagents for Chemical
Synthesis. Aldrichimica Acta 2015, 48, 59−70; (d) Wang, X.-N.; Yeom,
H.-S.; Fang, L.-C.; He, S.; Ma, Z.-X.; Kedrowski, B. L.; Hsung, R. P.
Ynamides in Ring Forming Transformations. Acc. Chem. Res. 2014, 47,
560−578; (e) DeKorver, K. A.; Li, H.; Lohse, A. G.; Hayashi, R.; Lu, Z.;
Zhang, Y.; Hsung, R. P. Ynamides: A Modern Functional Group for the
New Millennium. Chem. Rev. 2010, 110, 5064−5106; (f) Evano, G.;
Coste, A.; Jouvin, K. Ynamides: Versatile Tools in Organic Synthesis.
Angew. Chem. Int. Ed. 2010, 49, 2840−2859.
For selected examples by our group, see: (a) Hong, F.-L.; Wang, Z.-S.;
Wei, D.-D.; Zhai, T.-Y.; Deng, G.-C.; Lu, X.; Liu, R.-S.; Ye, L.-W.
Generation of Donor/Donor Copper Carbenes through
Copper-Catalyzed Diyne Cyclization: Enantioselective and Divergent
Synthesis of Chiral Polycyclic Pyrroles. J. Am. Chem. Soc. 2019, 141,
16961−16970; (b) Xu, Y.; Sun, Q.; Tan, T.-D.; Yang, M.-Y.; Yuan, P.;
Wu, S.-Q.; Lu, X.; Hong, X.; Ye, L.-W. Organocatalytic Enantioselective
Conia-Ene-Type Carbocyclization of Ynamide-Cyclohexanones:
Regiodivergent Synthesis of Morphans and Normorphans. Angew.
Chem. Int. Ed. 2019, 58, 16252−16259; (c) Li, L.; Zhu, X.-Q.; Zhang,
Y.-Q.; Bu, H.-Z.; Yuan, P.; Chen, J.; Su, J.; Deng, X.; Ye, L.-W.
Synthesis of a-Fluoroketones by Insertion of HF into a Gold Carbene.
Angew. Chem. Int. Ed. 2016, 55, 10032−10036; (h) Ji, K.; Liu, X.; Du, B.;
Yang, F.; Gao, J. Gold-catalyzed selective oxidation of
4-oxahepta-1,6-diynes
to
2H-pyran-3(6H)-ones
and
chromen-3(4H)-ones via β-gold vinyl cation intermediates. Chem.
Commun. 2015, 51, 10318−10321; (i) Zheng, Z.; Zhang, L. C–H
insertions in oxidative gold catalysis: synthesis of polycyclic
2H-pyran-3(6H)-ones via a relay strategy. Org. Chem. Front. 2015, 2,
1556−1560; (j) Li, L.; Shu, C.; Zhou, B.; Yu, Y.-F.; Xiao, X.-Y.; Ye, L.-W.
Generation of gold carbenes in water: efficient intermolecular
trapping of the α-oxo gold carbenoids by indoles and anilines. Chem.
Sci. 2014, 5, 4057−4064; (k) Shu, C.; Li, L.; Xiao, X.-Y.; Yu, Y.-F.; Ping,
Y.-F.; Zhou, J.-M.; Ye, L.-W. Flexible and Practical Synthesis of
3-Oxyindoles through Gold-Catalyzed Intermolecular Oxidation of
o-Ethynylanilines. Chem. Commun. 2014, 50, 8689−8692; (l) Nösel, P.;
dos Santos Comprido, L. N.; Lauterbach, T.; Rudolph, M.; Rominger,
F.; Hashmi, A. S. K. 1,6-Carbene Transfer: Gold-Catalyzed Oxidative
Diyne Cyclizations. J. Am. Chem. Soc. 2013, 135, 15662−15666.
(a) Zhu, B.-H.; Wang, C.-M.; Su, H.-Y.; Ye, L.-W. NaBArF -Catalyzed
4
Oxidative Cyclization of 1,5- and 1,6-Diynes: Efficient and Divergent
Synthesis of Functionalized γ- and δ-Lactams. Chin. J. Chem. 2019, 37,
58−62; (b) Wang, C.-M.; Qi, L.-J.; Sun, Q.; Zhou, B.; Zhang, Z.-X.; Shi,
Z.-F.; Lin, S.-C.; Lu, X.; Gong, L.; Ye, L.-W. Transition-metal-free
oxidative cyclization of N-propargyl ynamides: stereospecific
construction of linear polycyclic N-heterocycles. Green Chem. 2018,
20, 3271−3278; (c) Shen, W.-B.; Sun, Q.; Li, L.; Liu, X.; Zhou, B.; Yan,
J.-Z.; Lu, X.; Ye, L.-W. Divergent synthesis of N-heterocycles via
controllable cyclization of azido-diynes catalyzed by copper and gold.
Nat. Commun. 2017, 8, 1748; (d) Li, L.; Zhou, B.; Wang, Y.-H.; Shu, C.;
Pan, Y.-F.; Lu, X.; Ye, L.-W. Zinc-Catalyzed Alkyne Oxidation/C-H
Functionalization: Highly Site-Selective Synthesis of Versatile
Isoquinolones and β-Carbolines. Angew. Chem. Int. Ed. 2015, 54,
8245−8249.
(a) Zhu, J.; Ren, X.; Tang, F.; Pan, F.; Ye, L.-W. Synthesis of α-Halo
Amides via Zinc-Mediated Tandem Oxidation/Halogenation of
Ynamides. Chin. J. Org. Chem. 2019, 39, 1102−1108; (b) Zhang, Z.-X.;
Zhu, B.-H.; Xie, P.-X.; Tang, J.-Q.; Li, X.-L.; Zhu, C.-Y.; Yin, Y.-W.; Ye,
L.-W. Facile synthesis of α-alkoxyl amides via scandium-catalyzed
oxidative reaction between ynamides and alcohols. RSC Adv. 2018, 8,
18308−18315; (c) Ruan, P.-P.; Shen, C.-H.; Li, L.; Liu, C.-Y.; Ye, L.-W. A
zinc-catalyzed oxidative reaction of ynamides with phenols and
thiophenols: highly site-selective synthesis of versatile α-aryloxy
amides and α-arylthio amides. Org. Chem. Front. 2016, 3, 989−993;
(d) Pan, F.; Li, X.-L.; Chen, X.-M.; Shu, C.; Ruan, P.-P.; Shen, C.-H.; Lu,
X.; Ye, L.-W. Catalytic Ynamide Oxidation Strategy for the Preparation
of α-Functionalized Amides. ACS Catal. 2016, 6, 6055−6062.
Metal-Free
Alkene
Carbooxygenation
Following
Tandem
Intramolecular
Alkoxylation/Claisen
Rearrangement:
Stereocontrolled Access to Bridged [4.2.1] Lactones. Chem. Sci. 2019,
10, 3123−3129; (d) Shen, W.-B.; Zhou, B.; Zhang, Z.-X.; Yuan, H.; Fang,
W.; Ye, L.-W. Gold-catalyzed cascade cyclization of N-propargyl
ynamides: rapid access to functionalized indeno[1,2-c]pyrroles. Org.
Chem. Front. 2018, 5, 2468−2472; (e) Shen, W.-B.; Xiao, X.-Y.; Sun, Q.;
Zhou, B.; Zhu, X.-Q.; Yan, J.-Z.; Lu, X.; Ye, L.-W. Highly Site Selective
Formal [5+2] and [4+2] Annulations of Isoxazoles with
Heterosubstituted Alkynes by Platinum Catalysis: Rapid Access to
Functionalized 1,3-Oxazepines and 2,5-Dihydropyridines. Angew.
Chem. Int. Ed. 2017, 56, 605−609; (f) Li, L.; Chen, X.-M.; Wang, Z.-S.;
Zhou, B.; Liu, X.; Lu, X.; Ye, L.-W. Reversal of Regioselectivity in
Catalytic Arene-Ynamide Cyclization: Direct Synthesis of Valuable
Azepino[4,5-b]indoles and β-Carbolines and DFT Calculations. ACS
Catal. 2017, 7, 4004−4010; (g) Shu, C.; Shen, C.-H.; Wang, Y.-H.; Li, L.;
Li, T.; Lu, X.; Ye, L.-W. Synthesis of 2-Aza-1,3-butadienes through
Gold-Catalyzed
Intermolecular
Ynamide
Amination/C-H
Functionalization. Org. Lett. 2016, 18, 4630−4633; (h) Shu, C.; Wang,
Y.-H.; Shen, C.-H.; Ruan, P.-P.; Lu, X.; Ye, L.-W. Gold-Catalyzed
Intermolecular Ynamide Amination-Initiated Aza-Nazarov Cyclization:
Access to Functionalized 2-Aminopyrroles. Org. Lett. 2016, 18,
3254−3257; (i) Shu, C.; Wang, Y.-H.; Zhou, B.; Li, X.-L.; Ping, Y.-F.; Lu,
X.; Ye, L.-W. Generation of α-Imino Gold Carbenes through
Gold-Catalyzed Intermolecular Reaction of Azides with Ynamides. J.
Am. Chem. Soc. 2015, 137, 9567−9570; (j) Zhou, A.-H.; He, Q.; Shu, C.;
Yu, Y.-F.; Liu, S.; Zhao, T.; Zhang, W.; Lu, X.; Ye, L.-W. Atom-economic
generation of gold carbenes: gold-catalyzed formal [3+2]
cycloaddition between ynamides and isoxazoles. Chem. Sci. 2015, 6,
1265−1271.
(a) Zhou, B.; Zhang, Y.-Q.; Zhang, K.; Yang, M.-Y.; Chen, Y.-B.; Li, Y.;
Peng, Q.; Zhu, S.-F.; Zhou, Q.-L.; Ye, L.-W. Stereoselective synthesis of
medium
lactams
enabled
by
metal-free
hydroalkoxylation/stereospecific [1,3]-rearrangement. Nat. Commun.
2019, 10, 3234. (b) Zhou, B.; Li, L.; Zhu, X.-Q.; Yan, J.-Z.; Guo, Y.-L.; Ye,
L.-W. Yttrium-Catalyzed Intramolecular Hydroalkoxylation/Claisen
Rearrangement Sequence: Efficient Synthesis of Medium-Sized
Lactams. Angew. Chem. Int. Ed. 2017, 56, 4015−4019.
For recent reviews on ynamide reactivity, see: (a) Zhou, B.; Tan, T.-D.;
For Brønsted acid-catalyzed alkyne oxidations, see: (a) Zhang, Y.-Q.;
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