Selective Alkynylallylation of the C-C σ Bond of Cyclopropenes.
C−C bond cleavage
cyclopropene
dicarbofunctionalization
palladium
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
04 Jan 2021
04 Jan 2021
Historique:
received:
25
06
2020
revised:
12
08
2020
pubmed:
11
9
2020
medline:
11
9
2020
entrez:
10
9
2020
Statut:
ppublish
Résumé
A Pd-catalyzed regio- and stereoselective alkynylallylation of a specific C-C σ bond in cyclopropenes, using allyl propiolates as both allylation and alkynylation reagents, has been achieved for the first time. By merging selective C(sp
Identifiants
pubmed: 32909645
doi: 10.1002/anie.202008886
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
297-303Subventions
Organisme : National Basic Research Program of China (973 Program)
ID : 2018YFA0507900
Informations de copyright
© 2020 Wiley-VCH GmbH.
Références
For recent reviews:
J. Derosa, O. Apolinar, T. Kang, V. T. Tran, K. M. Engle, Chem. Sci. 2020, 11, 4287-4296;
R. K. Dhungana, S. Kc, P. Basnet, R. Giri, Chem. Rec. 2018, 18, 1314-1340.
For selected examples:
X. Y. Dong, J. T. Cheng, Y. F. Zhang, Z. L. Li, T. Y. Zhan, J. J. Chen, F. L. Wang, N. Y. Yang, L. Ye, Q. S. Gu, X. Y. Liu, J. Am. Chem. Soc. 2020, 142, 9501-9509;
S. Z. Sun, Y. Duan, R. S. Mega, R. J. Somerville, R. Martin, Angew. Chem. Int. Ed. 2020, 59, 4370-4374;
Angew. Chem. 2020, 132, 4400-4404;
M. Koy, P. Bellotti, F. Katzenburg, C. G. Daniliuc, F. Glorius, Angew. Chem. Int. Ed. 2020, 59, 2375-2379;
Angew. Chem. 2020, 132, 2395-2399;
M. W. Campbell, J. S. Compton, C. B. Kelly, G. A. Molander, J. Am. Chem. Soc. 2019, 141, 20069-20078;
Z. M. Zhang, B. Xu, L. Wu, Y. Wu, Y. Qian, L. Zhou, Y. Liu, J. Zhang, Angew. Chem. Int. Ed. 2019, 58, 14653-14659;
Angew. Chem. 2019, 131, 14795-14801;
W. Shu, A. García-Dominguez, M. T. Quiros, R. Mondal, D. J. Cardenas, C. Nevado, J. Am. Chem. Soc. 2019, 141, 13812-13821;
Y. Jin, C. Wang, Angew. Chem. Int. Ed. 2019, 58, 6722-6726;
Angew. Chem. 2019, 131, 6794-6798;
V. R. Yatham, Y. Shen, R. Martin, Angew. Chem. Int. Ed. 2017, 56, 10915-10919;
Angew. Chem. 2017, 129, 11055-11059;
B. Shrestha, P. Basnet, R. K. Dhungana, S. Kc, S. Thapa, J. M. Sears, R. Giri, J. Am. Chem. Soc. 2017, 139, 10653-10656;
J. Derosa, V. T. Tran, M. N. Boulous, J. S. Chen, K. M. Engle, J. Am. Chem. Soc. 2017, 139, 10657-10660;
A. Garcia-Dominguez, Z. Li, C. Nevado, J. Am. Chem. Soc. 2017, 139, 6835-6838;
S. Thapa, Basnet, P. R. Giri, J. Am. Chem. Soc. 2017, 139, 5700-5703;
Z. Liu, T. Zeng, K. S. Yang, K. M. Engle, J. Am. Chem. Soc. 2016, 138, 15122-15125;
Z. Li, A. Garcia-Dominguez, C. Nevado, Angew. Chem. Int. Ed. 2016, 55, 6938-6941;
Angew. Chem. 2016, 128, 7052-7055;
A. Reding, P. G. Jones, D. B. Werz, Angew. Chem. Int. Ed. 2018, 57, 10610;
Angew. Chem. 2018, 130, 10770.
For selected recent reviews:
M. Murakami, N. Chatani, Cleavage of Carbon-Carbon Single Bonds by Transition Metals, Wiley-VCH, Weinheim, 2015;
“C−C Bond Activation”: G. Dong, Topics in Current Chemistry, Vol. 346, Springer, Berlin, 2014;
L. Deng, G. Dong, Trends Chem. 2020, 2, 183-198;
P. Sivaguru, Z. Wang, G. Zanoni, X. Bi, Chem. Soc. Rev. 2019, 48, 2615-2656;
Z. Nairoukh, M. Cormier, I. Marek, Nat. Rev. Chem. 2017, 1, 0035;
G. Fumagalli, S. Stanton, J. F. Bower, Chem. Rev. 2017, 117, 9404-9432;
P. Chen, B. A. Billett, T. Tsukamoto, G. Dong, ACS Catal. 2017, 7, 1340-1360;
M. Murakami, N. Ishida, J. Am. Chem. Soc. 2016, 138, 13759-13769;
I. Marek, A. Masarwa, P. O. Delaye, M. Leibeling, Angew. Chem. Int. Ed. 2015, 54, 414-429;
Angew. Chem. 2015, 127, 424-439;
L. Souillart, N. Cramer, Chem. Rev. 2015, 115, 9410-9464;
F. Chen, T. Wang, N. Jiao, Chem. Rev. 2014, 114, 8613-8661;
C. H. Jun, Chem. Soc. Rev. 2004, 33, 610-618.
Other 1,2-difunctionalization of C−C σ bonds:
A. Fawcett, T. Biberger, V. K. Aggarwal, Nat. Chem. 2019, 11, 117-122;
Y. Yonezawa, T. Furuya, T. Aratani, S. Fijinami, K. Inomata, Y. Ukaji, Tetrahedron: Asymmetry 2014, 25, 936-943;
Y. Akai, T. Yamamoto, Y. Nagata, T. Ohmura, M. Suginome, J. Am. Chem. Soc. 2012, 134, 11092-11095;
T. Ohmura, H. Taniguchi, M. Suginome, Org. Lett. 2009, 11, 2880-2883;
T. Ohmura, H. Taniguchi, Y. Kondo, M. Suginome, J. Am. Chem. Soc. 2007, 129, 3518-3519;
S. M. Ma, J. L. Zhang, Y. J. Cai, L. H. Lu, J. Am. Chem. Soc. 2003, 125, 13954-13955; Lewis acid catalyzed bisarylation of C−C σ-bond:
B. Mondal, D. Das, J. Saha, Org. Lett. 2020, 22, 5115.
For selected recent reviews, see:
Y. Cohen, A. Cohen, I. Marek, Chem. Rev. 2020, 120, https://doi.org/10.1021/acs.chemrev.0c00167;
V. Pirenne, B. Muriel, J. Waser, Chem. Rev. 2020, 120, https://doi.org/10.1021/acs.chemrev.0c00109;
D. B. Werz, A. T. Biju, Angew. Chem. Int. Ed. 2020, 59, 3385-3398;
Angew. Chem. 2020, 132, 3410-3424;
P. Gopinath, S. Chandrasekaran, Curr. Org. Chem. 2019, 23, 276-312;
L. Dian, I. Marek, Chem. Rev. 2018, 118, 8415-8434;
T. F. Schneider, J. Kaschel, D. B. Werz, Angew. Chem. Int. Ed. 2014, 53, 5504-5523;
Angew. Chem. 2014, 126, 5608-5628.
For selected recent reviews, see:
R. Vicente, Chem. Rev. 2020, 120, https://doi.org/10.1021/acs.chemrev.0c00151;
R. Vicente, Synthesis 2016, 48, 2343-2360;
C. Song, J. Wang, Z. Xu, Acta Chim. Sinica 2015, 73, 1114-1146;
Z. B. Zhu, Y. Wei, M. Shi, Chem. Soc. Rev. 2011, 40, 5534-5563;
M. Rubin, M. Rubina, V. Gevorgyan, Chem. Rev. 2007, 107, 3117-3179;
J. M. Fox, N. Yan, Curr. Org. Chem. 2005, 9, 719-732;
F. L. Carter, V. L. Frampton, Chem. Rev. 1964, 64, 497-525.
D. K. Rayabarapu, J. A. Tunge, J. Am. Chem. Soc. 2005, 127, 13510-13511.
S. F. Pi, B. X. Tang, J. H. Li, Y. L. Liu, Y. Liang, Org. Lett. 2009, 11, 2309-2312;
Z. S. Chen, X. H. Duan, P. X. Zhou, S. Ali, J. Y. Luo, Y. M. Liang, Angew. Chem. Int. Ed. 2012, 51, 1370-1374;
Angew. Chem. 2012, 124, 1399-1403;
Z. Li, J. Zheng, W. Hu, J. Li, W. Wu, H. Jiang, Org. Chem. Front. 2017, 4, 1363-1366.
For selected reviews on decarboxylative cross-coupling reactions, see:
J. D. Weaver, A. Recio, A. J. Grenning, J. A. Tunge, Chem. Rev. 2011, 111, 1846-1913;
R. Shang, L. Liu, Sci. China: Chem. 2011, 54, 1670-1687;
N. Rodríguez, L. J. Goossen, Chem. Soc. Rev. 2011, 40, 5030-5048.
S. Lin, M. Li, Z. Dong, F. Liang, J. Zhang, Org. Biomol. Chem. 2014, 12, 1341-1350.
T. Matsushima, S. Kobayashi, S. Watanabe, J. Org. Chem. 2016, 81, 7799-7806.
For selected recent reviews, see:
A. Fürstner, Angew. Chem. Int. Ed. 2018, 57, 4215-4233;
Angew. Chem. 2018, 130, 4289-4308;
P. A. Inglesby, P. A. Evans, Chem. Soc. Rev. 2010, 39, 2791-2805;
E. Jiménez-Núñez, A. M. Echavarren, Chem. Rev. 2008, 108, 3326-3350;
V. Michelet, P. Y. Toullec, J.-P. Genêt, Angew. Chem. Int. Ed. 2008, 47, 4268-4315;
Angew. Chem. 2008, 120, 4338-4386;
C. Aubert, O. Buisine, M. Malacria, Chem. Rev. 2002, 102, 813-834.
For selected recent reviews, see:
J. Xuan, A. Studer, Chem. Soc. Rev. 2017, 46, 4329-4346;
U. Wille, Chem. Rev. 2013, 113, 813-853;
I. D. G. Watson, F. D. Toste, Chem. Sci. 2012, 3, 2899-2919.
For selected recent reviews, see:
A. Rahim, J. Feng, Z. Gu, Chin. J. Chem. 2019, 37, 929-945;
F. Shi, R. C. Larock, Top. Curr. Chem. 2010, 292, 123-164;
S. Ma, Z. Gu, Angew. Chem. Int. Ed. 2005, 44, 7512-7517;
Angew. Chem. 2005, 117, 7680-7685.
“Migratory Insertion Reactions”: J. F. Hartwig, Organotransition Metal Chemistry: From Bonding to Catalysis, University Science Books, Sausalito, 2010, chap. 9.
Deposition Numbers 1877510, 1968394, 1877506, 1971463, and 1968397 (for 3 a, 3 j, 3 u, 3 v, and 4 a) contains the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service www.ccdc.cam.ac.uk/structures.