Carbon-carbon bond forming reactions of acetylenic esters and ketones within frustrated phosphane/borane Lewis pair frameworks

被引:8
作者
Wang, Long [1 ,2 ,3 ]
Li, Jun [1 ]
Deng, Dongsheng [1 ]
Daniliuc, Constantin G. [1 ]
Mueck-Lichtenfeld, Christian [1 ]
Kehr, Gerald [1 ]
Erker, Gerhard [1 ]
机构
[1] Westfalische Wilhelms Univ Munster, Organ Chem Inst, Corrensstr 40, D-48149 Munster, Germany
[2] Huazhong Univ Sci & Technol, Sch Chem & Chem Engn, 1037 Luoyu Rd, Wuhan 430074, Hubei, Peoples R China
[3] Huazhong Univ Sci & Technol, Hubei Key Lab Bioinorgan Chem & Mat Med, 1037 Luoyu Rd, Wuhan 430074, Hubei, Peoples R China
基金
欧洲研究理事会;
关键词
RAY CRYSTAL-STRUCTURE; ONE-POT SYNTHESIS; DIHYDROGEN ACTIVATION; HYDROBORATION; CHEMISTRY; BIS(PENTAFLUOROPHENYL)BORANE; TRIPHENYLPHOSPHINE; DERIVATIVES; PHOSPHINES; BEARING;
D O I
10.1039/c9dt02624j
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The three-component reactions of bulky diarylbutenylphosphanes with dimethyl acetylenedicarboxylate (1a) and the strong boron Lewis acid B(C6F5)(3) give the ylide-substituted cyclopropane derivatives 26. The acetylenic ester 1a and ketone 1b react with oligomethylene bridged frustrated phosphane/borane Lewis pairs to give the bicyclic C-H insertion/C-C coupling reaction products. The formal carbene products are formed by means of stepwise sequences involving polar intermediate.
引用
收藏
页码:11921 / 11926
页数:6
相关论文
共 33 条
[1]   A novel, one-pot and three-component synthesis of α-quinoxalinyl triphenylphosphoranes [J].
Adib, Mehdi ;
Sheibani, Esmaeil ;
Abbasi, Alireza ;
Bijanzadeh, Hamid Reza .
TETRAHEDRON LETTERS, 2007, 48 (07) :1179-1182
[2]  
Aitken RA, 2003, EUR J ORG CHEM, V2003, P623
[3]   X-RAY CRYSTAL-STRUCTURE OF THE BORON-STABILIZED CARBANION - [LI(12-CROWN-4)2][CH2C6H2(3,5-ME2)(4-B(2,4,6-ME3C6H2)2)].ET2O - EVIDENCE FOR BORON YLIDE CHARACTER [J].
BARTLETT, RA ;
POWER, PP .
ORGANOMETALLICS, 1986, 5 (09) :1916-1917
[4]   STUDIES OF THE REACTION OF TRIVALENT PHOSPHORUS-COMPOUNDS WITH DIALKYL ACETYLENEDICARBOXYLATES IN THE PRESENCE OF CARBON-DIOXIDE [J].
CAESAR, JC ;
GRIFFITHS, DV ;
GRIFFITHS, PA ;
TEBBY, JC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (12) :2425-2430
[5]   Phospha-Claisen Type Reactions at Frustrated Lewis Pair Frameworks [J].
Chen, Guo-Qiang ;
Kehr, Gerald ;
Mueck-Lichtenfeld, Christian ;
Daniliuc, Constantin G. ;
Erker, Gerhard .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (27) :8554-8559
[6]   Synthesis and chemistry of fullerene derivatives bearing phosphorus substituents.: Unusual reaction of phosphines with electron-deficient acetylenes and C60 [J].
Chuang, SC ;
Santhosh, KC ;
Lin, CH ;
Wang, SL ;
Cheng, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18) :6664-6669
[7]   Cyclopropanation/Carboboration Reactions of Enynes with B(C6F5)3 [J].
Hansmann, Max M. ;
Melen, Rebecca L. ;
Rudolph, Matthias ;
Rominger, Frank ;
Wadepohl, Hubert ;
Stephan, Douglas W. ;
Hashmi, A. Stephen K. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (49) :15469-15477
[8]   Generation of bis(pentafluorophenyl)borane-dimethyl sulfide complex as a solution of hexane and its application to hydroboration of alk-1-yne with pinacolborane [J].
Hoshi, Masayuki ;
Shirakawa, Kazuya ;
Okirnoto, Mitsuhiro .
TETRAHEDRON LETTERS, 2007, 48 (48) :8475-8478
[9]   An efficient and rapid one-pot synthesis of highly functionalized stable phosphorus ylides containing the sulfur atom [J].
Islami, MR ;
Hassani, Z ;
Saidi, K .
SYNTHETIC COMMUNICATIONS, 2003, 33 (01) :65-72
[10]   ADDUCTS FROM TRIPHENYLPHOSPHINE AND DIMETHYL ACETYLENEDICARBOXYLATE [J].
JOHNSON, AW ;
TEBBY, JC .
JOURNAL OF THE CHEMICAL SOCIETY, 1961, (MAY) :2126-&