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TitleLigand-Controlled Regiodivergent Nickel-Catalyzed Hydrocyanation of Silyl-Substituted 1,3-Diynes
Author (Name in English or Pinyin)
Sun, Feilong1; Yang, Chengxi2; Ni, Jie2; Cheng, Gui-Juan2; Fang, Xianjie1
Date Issued2021-05-21
Source PublicationORGANIC LETTERS
ISSN1523-7060
DOI10.1021/acs.orglett.1c01262
Indexed BySCIE
Firstlevel Discipline化学
Education discipline科技类
Published range国外学术期刊
Volume Issue Pages卷: 23 期: 10 页: 4045-4050
References
[1] Chen, G.; Wang, L.; Thompson, D. W.; Zhao, Y. Highly π-Extended TTF analogues with a conjugated macrocyclic enyne core. Org. Lett. 2008, 10, 657-660, 10.1021/ol703038m
[2] Ma, X.; Banwell, M. G.; Willis, A. C. Chemoenzymatic total synthesis of the phytotoxic geranylcyclohexentriol (-)-Phomentrioloxin. J. Nat. Prod. 2013, 76, 1514-1518, 10.1021/np4002866
[3] For selected examples, see: Huang, Y.; delPozo, J.; Torker, S.; Hoveyda, A. H. Enantioselective synthesis of trisubstituted allenyl-B(pin) compounds by phosphine-Cu-catalyzed 1,3-enyne hydroboration. Insights regarding stereochemical integrity of Cu-allenyl intermediates. J. Am. Chem. Soc. 2018, 140, 2643-2655, 10.1021/jacs.7b13296
[4] Bharathiraja, G.; Sathishkannan, G.; Punniyamurthy, T. Domino synthesis of tetrasubstituted thiophenes from 1,3-enynes with mercaptoacetaldehyde. J. Org. Chem. 2016, 81, 2670-2674, 10.1021/acs.joc.6b00231
[5] Li, W.; Yu, X.; Yue, Z.; Zhang, J. Asymmetric construction of 2,3-dihydroisoxazoles via an organocatalytic formal [3 + 2] cycloaddition of enynes with N-hydroxylamines. Org. Lett. 2016, 18, 3972-3975, 10.1021/acs.orglett.6b01737
[6] Wang, Y.; Zhang, Z.-M.; Liu, F.; He, Y.; Zhang, J. Ming-phos/gold(I)-catalyzed diastereo-and enantioselective synthesis of indolyl-substituted cyclopenta[c]furans. Org. Lett. 2018, 20, 6403-6406, 10.1021/acs.orglett.8b02701
[7] Bharathiraja, G.; Sakthivel, S.; Sengoden, M.; Punniyamurthy, T. A novel tandem sequence to pyrrole syntheses by 5-endo-dig cyclization of 1,3-enynes with amines. Org. Lett. 2013, 15, 4996-4999, 10.1021/ol402305b
[8] Poulsen, P. H.; Li, Y.; Lauridsen, V. H.; Jørgensen, D. K. B.; Palazzo, T. A.; Meazza, M.; Jørgensen, K. A. Organocatalytic formation of chiral trisubstituted allenes and chiral furan derivatives. Angew. Chem., Int. Ed. 2018, 57, 10661-10665, 10.1002/anie.201806238
[9] Li, W.; Zhang, J. Phosphine-mediated regio-and stereoselective hydrocarboxylation of enynes. Org. Lett. 2014, 16, 162-165, 10.1021/ol4031556
[10] El-Kemary, M.; Organero, J. A.; Douhal, A. Fast relaxation dynamics of the cardiotonic drug milrinone in water solutions. J. Med. Chem. 2006, 49, 3086-3091, 10.1021/jm0600038
[11] Chen, Z.; Zhang, J. Highly functionalized 4-alkylidenebicyclo[3.1.0]hex-2-enes by tandem michael addition and annulation of electron-deficient enynes. Chem.-Asian J. 2009, 4, 1527-1529, 10.1002/asia.200900290
[12] Yu, X.; Zhou, G.; Zhang, J. DBU-catalyzed tandem additions of electron-deficient 1,3-conjugated enynes with 2-aminomalonates: a facile access to highly substituted 2-pyrrolines. Chem. Commun. 2012, 48, 4002-4004, 10.1039/c2cc30840a
[13] Liu, J.; Schneider, C.; Yang, J.; Wei, Z.; Jiao, H.; Franke, R.; Jackstell, R.; Beller, M. A general and highly selective palladium-catalyzed hydroamidation of 1,3-Diynes. Angew. Chem., Int. Ed. 2021, 60, 371-379, 10.1002/anie.202010768
[14] Liu, J.; Yang, J.; Schneider, C.; Franke, R.; Jackstell, R.; Beller, M. Tailored palladium catalysts for selective synthesis of conjugated enynes by monocarbonylation of 1,3-diynes. Angew. Chem., Int. Ed. 2020, 59, 9032-9040, 10.1002/anie.201915386
[15] Liu, J.; Yang, J.; Baumann, W.; Jackstell, R.; Beller, M. Stereoselective synthesis of highly substituted conjugated dienes via Pd-catalyzed carbonylation of 1,3-diynes. Angew. Chem., Int. Ed. 2019, 58, 10683-10687, 10.1002/anie.201903533
[16] Sang, H. L.; Wu, C.; Phua, G. G. D.; Ge, S. Cobalt-catalyzed regiodivergent stereoselective hydroboration of 1,3-diynes to access boryl-functionalized enynes. ACS Catal. 2019, 9, 10109-10114, 10.1021/acscatal.9b03139
[17] Sang, H. L.; Hu, Y.; Ge, S. Cobalt-catalyzed regio-and stereoselective hydrosilylation of 1,3-diynes to access silyl-functionalized 1,3-enynes. Org. Lett. 2019, 21, 5234-5237, 10.1021/acs.orglett.9b01836
[18] Li, D.; Kim, Y. E.; Yun, J. Highly regio-and stereoselective synthesis of boron-substituted enynes via copper-catalyzed borylation of conjugated diynes. Org. Lett. 2015, 17, 860-863, 10.1021/ol503720w
[19] Cho, C.-W.; Krische, M. J. α-hydroxy esters via enantioselective hydrogen-mediated C-C coupling: regiocontrolled reactions of silyl-substituted 1,3-Diynes. Org. Lett. 2006, 8, 3873-3876, 10.1021/ol061485k
[20] Sun, F.; Ni, J.; Cheng, G.-J.; Fang, X. Highly region-and stereoselective Ni-catalyzed hydrocyanation of 1,3-enynes. Chem.-Eur. J. 2020, 26, 5956-5960, 10.1002/chem.202000651
[21] Sun, F.; Gao, J.; Fang, X. Direct access to pentenedinitriles via Ni-catalyzed dihydrocyanation of 1,3-enynes. Chem. Commun. 2020, 56, 6858-6861, 10.1039/D0CC02938F
[22] For selected reviews: Rajanbabu, T. V. Hydrocyanation of Alkenes and Alkynes. In Organic Reactions; John Wiley & Sons, Inc.: Hoboken, NJ, 2011; Vol. 75, Chapter 1, pp 1-74.
[23] Fallon, G. D.; Fitzmaurice, N. J.; Jackson, W. R.; Perlmutter, P. J. Regio-and stereo-chemical control in the nickel-catalysed addition of HCN to alkynes. A simple synthesis of (E)-2-alkyl-3-trialkylsilylalk-2-enenitriles. J. Chem. Soc., Chem. Commun. 1985, 4-5, 4, 10.1039/c39850000004
[24] Campi, E. M.; Jackson, W. R. The stereochemistry of organometallic compounds. XXXIII. Preparation and reactions of some substituted buta-1,3-dienes. Aust. J. Chem. 1989, 42, 471-478, 10.1071/CH9890471
[25] Debrauwer, V.; Turlik, A.; Rummler, L.; Prescimone, A.; Blanchard, N.; Houk, K. N.; Bizet, V. Ligand-controlled regiodivergent palladium-catalyzed hydrogermylation of ynamides. J. Am. Chem. Soc. 2020, 142, 11153-11164, 10.1021/jacs.0c03556
[26] Noonan, G. M.; Fuentes, J. A.; Cobley, C. J.; Clarke, M. L. An asymmetric hydroformylation catalyst that delivers branched aldehydes from alkyl alkenes. Angew. Chem., Int. Ed. 2012, 51, 2477-2480, 10.1002/anie.201108203
[27] Dingwall, P.; Fuentes, J. A.; Crawford, L.; Slawin, A. M. Z.; Bühl, M.; Clarke, M. L. Understanding a hydroformylation catalyst that produces branched aldehydes from alkyl alkenes. J. Am. Chem. Soc. 2017, 139, 15921-15932, 10.1021/jacs.7b09164
[28] Chatani, N.; Amishiro, N.; Murai, S. A new catalytic reaction involving oxidative addition of iodotrimethylsilane (Me3SiI) to palladium (0). Synthesis of stereodefined enynes by the coupling of Me3SiI, acetylenes, and acetylenic tin reagents. J. Am. Chem. Soc. 1991, 113, 7778-7780, 10.1021/ja00020a060
[29] Xing, Y.; Yu, R.; Fang, X. Synthesis of tertiary benzylic nitriles via nickel-catalyzed markovnikov hydrocyanation of α-substituted styrenes. Org. Lett. 2020, 22, 1008-1012, 10.1021/acs.orglett.9b04554
[30] Kong, H.-H.; Pan, H.-L.; Ding, M.-W. Synthesis of 2-tetrazolyl-substituted 3-acylpyrroles via a sequential ugi-azide/Ag-catalyzed oxidative cycloisomerization reaction. J. Org. Chem. 2018, 83, 12921-12930, 10.1021/acs.joc.8b01984
Citation statistics
Cited Times:13[WOS]   [WOS Record]     [Related Records in WOS]
Document TypeJournal article
Identifierhttps://irepository.cuhk.edu.cn/handle/3EPUXD0A/2188
CollectionSchool of Medicine
Co-First AuthorYang, Chengxi
Corresponding AuthorCheng, Gui-Juan; Fang, Xianjie
Affiliation
1.Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Sch Chem & Chem Engn, Shanghai Key Lab Mol Engn Chiral Drugs, Shanghai 200240, Peoples R China
2.Chinese Univ Hong Kong Shenzhen , Sch Life & Hlth Sci, Warshel Inst Computat Biol, Shenzhen Key Lab Steroid Drug Discovery & Dev, Shenzhen 518172, Peoples R China
Corresponding Author AffilicationThe Chinese University of HongKong,Shenzhen
Recommended Citation
GB/T 7714
Sun, Feilong,Yang, Chengxi,Ni, Jieet al. Ligand-Controlled Regiodivergent Nickel-Catalyzed Hydrocyanation of Silyl-Substituted 1,3-Diynes[J]. ORGANIC LETTERS,2021.
APA Sun, Feilong, Yang, Chengxi, Ni, Jie, Cheng, Gui-Juan, & Fang, Xianjie. (2021). Ligand-Controlled Regiodivergent Nickel-Catalyzed Hydrocyanation of Silyl-Substituted 1,3-Diynes. ORGANIC LETTERS.
MLA Sun, Feilong,et al."Ligand-Controlled Regiodivergent Nickel-Catalyzed Hydrocyanation of Silyl-Substituted 1,3-Diynes".ORGANIC LETTERS (2021).
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