N-Geminal P/Al Lewis Pair-Alkyne Dipolar Cycloaddition to the Zwitterionic C2PNAl-Heterocyclopentene

被引：7

作者：

Ding, Shuang ^{[1
]}

Li, Jiancheng ^{[1
]}

Liu, Rui ^{[1
]}

Fu, Gang ^{[1
]}

Zhu, Hongping ^{[1
]}

Liu, Weiping ^{[2
]}

Ye, Qingsong ^{[2
]}

机构：

[1] Xiamen Univ, State Key Lab Phys Chem Solid Surfaces, Natl Engn Lab Green Chem Prod Alcohols Ethers Est, Coll Chem & Chem Engn, Xiamen 361005, Peoples R China

[2] Kunming Inst Precious Met, State Key Lab Platinum Grp Met, Kunming 650106, Yunnan, Peoples R China

来源：

ACS OMEGA | 2017年 / 2卷 / 06期

关键词：

RAY CRYSTAL-STRUCTURES; MOLECULAR-STRUCTURE; AMPHOTERIC LIGANDS; ADDITION-REACTIONS; PHOSPHINE-LIGANDS; ADDUCT FORMATION; CLICK CHEMISTRY; ACTIVATION; ALUMINUM; TRIMETHYLALUMINUM;

D O I：

10.1021/acsomega.7b00236

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The N-geminal P/ Al Lewis pair [Ph2PN(2,6iPr2C6H3) AlEt2] 2 (1) has been prepared and studied for reaction with a series of alkynes. The reaction of 1 with RC. CR yielded zwitterionic C2PNAl-heterocyclopentene [Ph2PN( 2,6-iPr2C6H3) AlEt2](CR. CR) (R = Me (2), Ph (3)); with PhC. CEt produced two isomers, [Ph2PN(2,6-iPr2C6H3) AlEt2](CPh. CEt) (4a) and [Ph2PN(2,6-iPr2C6H3) AlEt2](CEt. CPh) (4b); and with other alkynes generated [Ph2PN(2,6-iPr2C6H3) AlEt2](CR1. CR2) (R1, R2 = CO 2 Et, Ph (5); SiMe3, Ph (6); PPh2, Ph (7); SiMe3, H (8); H, EtO (9)). Natural bond orbital analysis of the charge separation of the C. C bond of alkynes was carried out, and then, the electronic matching interaction mode between the combined Lewis acid (AlEt2) and base (PPh2) groups of 1 and the C. C bond of such alkynes was discussed. Reactions of 1 with alkene, nitrile, and carbodiimide molecules were also carried out, and cycloaddition compounds 10-12 were produced.

引用

页码：2405 / 2414

页数：10

共 44 条

[1] MOLECULAR-STRUCTURE OF COMPLEX TRIMETHYLALUMINUM TRIMETHYLPHOSPHANE, (CH3)3AIP(CH3)3, DETERMINED BY GAS-PHASE ELECTRON-DIFFRACTION [J].

ALMENNINGEN, A ;

FERNHOLT, L ;

HAALAND, A ;

WEIDLEIN, J .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1978, 145 (01) :109-119

[2] Peptidomimetics via copper-catalyzed azide-alkyne cycloadditions [J].

Angell, Yu L. ;

Burgess, Kevin .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (10) :1674-1689

[3] Geminal Phosphorus/Aluminum-Based Frustrated Lewis Pairs: C-H versus C≡C Activation and CO2 Fixation [J].

Appelt, Christian ;

Westenberg, Hauke ;

Bertini, Federica ;

Ehlers, Andreas W. ;

Slootweg, J. Chris ;

Lammertsma, Koop ;

Uhl, Werner .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (17) :3925-3928

[4] Reactivity of Dimeric P/Al-Based Lewis Pairs toward Carbon Dioxide and tert-Butyl Isocyanate [J].

Bertini, Federica ;

Hoffmann, Frank ;

Appelt, Christian ;

Uhl, Werner ;

Ehlers, Andreas W. ;

Slootweg, J. Chris ;

Lammertsma, Koop .

ORGANOMETALLICS, 2013, 32 (22) :6764-6769

[5] THE REVERSIBLE ADDUCT FORMATION OF GROUP-III TRIALKYLS WITH RELATIVELY INVOLATILE PHOSPHINES - X-RAY CRYSTAL-STRUCTURES OF (ME3M)2.(PH2PCH2)2 (M = AL, GA, IN) AND (ME3AL)3.(PH2PCH2CH2)2PPH [J].

BRADLEY, DC ;

CHUDZYNSKA, H ;

FAKTOR, MM ;

FRIGO, DM ;

HURSTHOUSE, MB ;

HUSSAIN, B ;

SMITH, LM .

POLYHEDRON, 1988, 7 (14) :1289-1298

[6] [(NHC)2Cu]X Complexes as Efficient Catalysts for Azide-Alkyne Click Chemistry at Low Catalyst Loadings [J].

Diez-Gonzalez, Silvia ;

Nolan, Steven P. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (46) :8881-8884

[7] Deprotonation and Addition Reactions of Frustrated Lewis Pairs with Alkynes [J].

Dureen, Meghan A. ;

Brown, Christopher C. ;

Stephan, Douglas W. .

ORGANOMETALLICS, 2010, 29 (23) :6594-6607

[8] Terminal Alkyne Activation by Frustrated and Classical Lewis Acid/Phosphine Pairs [J].

Dureen, Meghan A. ;

Stephan, Douglas W. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (24) :8396-+

[9] Ethene/alkyne exchange reaction at an intramolecular frustrated Lewis pair [J].

Eller, Christina ;

Bussmann, Kathrin ;

Kehr, Gerald ;

Wibbeling, Birgit ;

Daniliuc, Constantin G. ;

Erker, Gerhard .

CHEMICAL COMMUNICATIONS, 2014, 50 (16) :1980-1982

[10] Stannylene-Based Lewis Pairs [J].

Freitag, Sarah ;

Krebs, Kilian M. ;

Henning, Jens ;

Hirdler, Janina ;

Schubert, Hartmut ;

Wesemann, Lars .

ORGANOMETALLICS, 2013, 32 (22) :6785-6791

← 1 2 3 4 5 →