Citation: Ying-Wei Zhao, Qiang Feng, Qiu-Ling Song. Copper-catalyzed decarboxylative hydroboration of phenylpropiolic acids under ligand-free or both ligand- and base-free conditions[J]. Chinese Chemical Letters, 2016, 27(4): 571-574.
Copper-catalyzed decarboxylative hydroboration of phenylpropiolic acids under ligand-free or both ligand- and base-free conditions
-
关键词:
- Decarboxylation
- / Hydroboration
- / Ligand-free
- / Base-free
- / Copper-catalysis
English
Copper-catalyzed decarboxylative hydroboration of phenylpropiolic acids under ligand-free or both ligand- and base-free conditions
-
Key words:
- Decarboxylation
- / Hydroboration
- / Ligand-free
- / Base-free
- / Copper-catalysis
-
-
[1] B. Carboni, L. Monnier, Recent developments in the chemistry of amine- and phosphine-boranes, Tetrahedron 55(1999) 1197-1248.
-
[2] (a) H.C. Brown, T. Hamaoka, N. Ravindran, Reaction of alkenylboronic acids with iodine under the influence of base. Simple procedure for the stereospecific conversion of terminal alkynes into trans-1-alkenyl iodides via hydroboration, J. Am. Chem. Soc. 95(1973) 5786-5788;
-
[3]
(b) G.A. Molander, N.M. Ellis, Highly stereoselective synthesis of cis-alkenyl pinacolboronates and potassium cis-alkenyltrifluoroborates via a hydroboration/protodeboronation approach, J. Org. Chem. 73(2008) 6841-6844;
-
[4]
(c) R.E. Shade, A.M. Hyde, J.C. Olsen, C.A. Merlic, Copper-promoted coupling of vinyl boronates and alcohols:a mild synthesis of allyl vinyl ethers, J. Am. Chem. Soc. 132(2010) 1202-1203;
-
[5]
(d) P.J. Riss, S. Lu, S. Telu, F.I. Aigbirhio, V.W. Pike, CuI-catalyzed 11C carboxylation of boronic acid esters:a rapid and convenient entry to 11C-labeled carboxylic acids, esters, and amides, Angew. Chem. Int. Ed. 51(2012) 2698-2702;
-
[6]
(e) N.R. Candeias, F. Montalbano, P.M.S.D. Cal, P.M.P. Gois, Boronic acids and esters in the Petasis-borono Mannich multicomponent reaction, Chem. Rev. 110(2010) 6169-6193;
-
[7]
(f) M. Tredwell, S.M. Preshlock, N.J. Taylor, et al., A general copper-mediated nucleophilic 18F fluorination of arenes, Angew. Chem. Int. Ed. 53(2014) 7751-7755.
-
[3] (a) Y.D. Bidal, F. Lazreg, C.S.J. Cazin, Copper-catalyzed regioselective formation of Tri- and tetrasubstituted vinylboronates in air, ACS Catal. 4(2014) 1564-1569;
-
[9]
(b) C. Gunanathan, M. Hö lscher, F. Pan, W. Leitner, Ruthenium catalyzed hydroboration of terminal alkynes to Z-vinylboronates, J. Am. Chem. Soc. 134(2012) 14349-14352.
-
[4] K. Takahashi, T. Ishiyama, N. Miyaura, A borylcopper species generated from bis(pinacolato)diboron and its additions to α,β-unsaturated carbonyl compounds and terminal alkynes, J. Organomet. Chem. 625(2001) 47-53.
-
[5] (a) J.E. Lee, J. Kwon, J. Yun, Copper-catalyzed addition of diboron reagents to[small alpha],[small beta]-acetylenic esters:efficient synthesis of β-boryl-α,bethylenic esters, Chem. Commun. (2008) 733-734;
-
[12]
(b) H.R. Kim, I.G. Jung, K. Yoo, et al., Bis(imidazoline-2-thione)-copper(i) catalyzed regioselective boron addition to internal alkynes, Chem. Commun. 46(2010) 758-760;
-
[13]
(c) H.R. Kim, J. Yun, Highly regio- and stereoselective synthesis of alkenylboronic esters by copper-catalyzed boron additions to disubstituted alkynes, Chem. Commun. 47(2011) 2943-2945;
-
[14]
(d) H.Y. Jung, J. Yun, Copper-catalyzed double borylation of silylacetylenes:highly regio- and stereoselective synthesis of syn-vicinal diboronates, Org. Lett. 14(2012) 2606-2609;
-
[15]
(e) J. Yun, Copper(I)-catalyzed boron addition reactions of alkynes with diboron reagents, Asian J. Org. Chem. 2(2013) 1016-1025.
-
[6] J. Zhao, Z. Niu, H. Fu, Y. Li, Ligand-free hydroboration of alkynes catalyzed by heterogeneous copper powder with high efficiency, Chem. Commun. 50(2014) 2058-2060.
-
[7] (a) H. Jang, A.R. Zhugralin, Y. Lee, A.H. Hoveyda, Highly selective methods for synthesis of internal (α-) vinylboronates through efficient NHC-Cu-catalyzed hydroboration of terminal alkynes. Utility in chemical synthesis and mechanistic basis for selectivity, J. Am. Chem. Soc. 133(2011) 7859-7871;
-
[18]
(b) Y. Lee, H. Jang, A.H. Hoveyda, Vicinal diboronates in high enantiomeric purity through tandem site-selective NHC-Cu-catalyzed boron-copper additions to terminal alkynes, J. Am. Chem. Soc. 131(2009) 18234-18235.
-
[8] (a) W. Yuan, S. Ma, CuCl-K2CO3-catalyzed highly selective borylcupration of internal alkynes-ligand effect, Org. Biomol. Chem. 10(2012) 7266-7268;
-
[20]
(b) K. Semba, T. Fujihara, J. Terao, Y. Tsuji, Copper-catalyzed highly regio-and stereoselective directed hydroboration of unsymmetrical internal alkynes:controlling regioselectivity by choice of catalytic species, Chem. Eur. J. 18(2012) 4179-4184;
-
[21]
(c) A.L. Moure, R. Gómez Arrayás, D.J. Cárdenas, I. Alonso, J.C. Carretero, Regiocontrolled CuI-catalyzed borylation of propargylic-functionalized internal alkynes, J. Am. Chem. Soc. 134(2012) 7219-7222.
-
[9] (a) W. Jia, N. Jiao, Cu-Catalyzed oxidative amidation of propiolic acids under air via decarboxylative coupling, Org. Lett. 12(2010) 2000-2003;
-
[23]
(b) D.L. Priebbenow, P. Becker, C. Bolm, Copper-catalyzed oxidative decarboxylative couplings of sulfoximines and aryl propiolic acids, Org. Lett. 15(2013) 6155-6157;
-
[24]
(c) X. Li, F. Yang, Y. Wu, Y. Wu, Copper-mediated oxidative decarboxylative coupling of arylpropiolic acids with dialkyl H-phosphonates in water, Org. Lett. 16(2014) 992-995;
-
[25]
(d) D. Zhao, C. Gao, X. Su, et al., Copper-catalyzed decarboxylative cross-coupling of alkynyl carboxylic acids with aryl halides, Chem. Commun. 46(2010) 9049-9051;
-
[26]
(e) L. Zhang, Z. Hang, Z.Q. Liu, A free-radical-promoted stereospecific decarboxylative silylation of α,β-unsaturated acids with silanes, Angew. Chem. Int. Ed. 55(2016) 236-239.
-
[10] (a) Q. Song, Q. Feng, M. Zhou, Copper-catalyzed oxidative decarboxylative arylation of benzothiazoles with phenylacetic acids and (α-hydroxyphenylacetic acids with O2 as the sole oxidant, Org. Lett. 15(2013) 5990-5993;
-
[28]
(b) Q. Feng, Q. Song, Copper-catalyzed decarboxylative C-N triple bond formation:direct synthesis of benzonitriles from phenylacetic acids under O2 atmosphere, Adv. Synth. Catal. 356(2014) 1697-1702;
-
[29]
(c) Q. Feng, Q. Song, Aldehydes and ketones formation:copper-catalyzed aerobic oxidative decarboxylation of phenylacetic acids and (α-hydroxyphenylacetic acids, J. Org. Chem. 79(2014) 1867-1871;
-
[30]
(d) Q. Song, Q. Feng, K. Yang, Synthesis of primary amides via copper-catalyzed aerobic decarboxylative ammoxidation of phenylacetic acids and α-hydroxyphenylacetic acids with ammonia in water, Org. Lett. 16(2014) 624-627.
-
[11] M. Zhou, M. Chen, Y. Zhou, et al., β-Ketophosphonate formation via aerobic oxyphosphorylation of alkynes or alkynyl carboxylic acids with H-phosphonates, Org. Lett. 17(2015) 1786-1789.
-
[12] Q. Feng, K. Yang, Q. Song, Highly selective copper-catalyzed trifunctionalization of alkynyl carboxylic acids:an efficient route to bis-deuterated β-borylated α,β-styrene, Chem. Commun. 51(2015) 15394-15397.
-
计量
- PDF下载量: 0
- 文章访问数: 757
- HTML全文浏览量: 25