Highly Selective Insertion of Arynes into a C(sp)-O(sp3) σ Bond

被引：36

作者：

Laczkowski, Krzysztof Z.

Garcia, Diego

Pena, Diego ^{[1
]}

Cobas, Agustin

Perez, Dolores

Guitian, Enrique

机构：

[1] Univ Santiago de Compostela, Dept Quim Organ, Santiago De Compostela 15782, Spain

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 05期

关键词：

TERMINAL ALKYNES; BENZYNE; PRECURSORS;

D O I：

10.1021/ol103001k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Arynes react with ethoxyacetylene to afford 2-ethoxyethynylaryl derivatives through a highly chemo- and regioselective formal insertion of the aryne into the C(sp)-O(sp(3)) bond of the alkyne. Computational studies suggest that the reaction does not proceed through a mechanism initiated by the nucleophilic addition of the oxygen atom to the aryne as previously proposed but by the addition of the triple bond of the alkyne to the aryne.

引用

页码：960 / 963

页数：4

共 34 条

[1] Reaction of benzyne with styrene oxide:: Insertion of arynes into a C-O bond of epoxides
Beltran-Rodil, Sandra
Pena, Diego
Guitian, Enrique
[J]. SYNLETT, 2007, (08) : 1308 - 1310
[2] Copper-catalyzed three-component coupling of arynes, terminal alkynes and activated alkenes
Bhuvaneswari, Sivakolundu
Jeganmohan, Masilamani
Cheng, Chien-Hong
[J]. CHEMICAL COMMUNICATIONS, 2008, (40) : 5013 - 5015
[3] Guitián E, 2005, TOP ORGANOMETAL CHEM, V14, P109
[4] FLUORIDE-INDUCED 1,2-ELIMINATION OF ORTHO-TRIMETHYLSILYLPHENYL TRIFLATE TO BENZYNE UNDER MILD CONDITIONS
HIMESHIMA, Y
SONODA, T
KOBAYASHI, H
[J]. CHEMISTRY LETTERS, 1983, (08) : 1211 - 1214
[5] Hoffmann R.W., 1967, DEHYDROBENZENE CYCLO
[6] O-Dihaloarenes as aryne precursors for nickel-catalyzed [2+2+2]cycloaddition with alkynes and nitriles
Hsieh, Jen-Chieh
Cheng, Chien-Hong
[J]. CHEMICAL COMMUNICATIONS, 2008, (26) : 2992 - 2994
[7] Expanding Pd-catalyzed C-N bond-forming processes: The first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions
Huang, XH
Anderson, KW
Zim, D
Jiang, L
Klapars, A
Buchwald, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (22) : 6653 - 6655
[8] A novel multicomponent reaction of arynes, β-keto sulfones, and Michael-type acceptors:: A direct synthesis of polysubstituted naphthols and naphthalenes
Huang, Xian
Xue, Jian
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (10) : 3965 - 3968
[9] SYNTHETIC APPROACHES TOWARD SPIRO[2,3-DIHYDRO-4H-1-BENZOPYRAN-4,1'-CYCLOHEXAN]-2-ONE DERIVATIVES VIA RADICAL REACTIONS - TOTAL SYNTHESIS OF (+/-)-LYCORAMINE
ISHIZAKI, M
OZAKI, K
KANEMATSU, A
ISODA, T
HOSHINO, O
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15) : 3877 - 3885
[10] JEGANMOHAN M, 2008, ANGEW CHEM INT EDIT, V47, P1

← 1 2 3 4 →