Ligand-Free, Palladium-Catalyzed Dihydrogen Generation from TMDS: Dehalogenation of Aryl Halides on Water

被引:57
作者
Bhattacharjya, Anish [1 ]
Klumphu, Piyatida [1 ]
Lipshutz, Bruce H. [1 ]
机构
[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
关键词
ROOM-TEMPERATURE HYDRODEHALOGENATION; REDUCTIVE DEHALOGENATION; ELECTRON-TRANSFER; AMPHIPHILE; COUPLINGS;
D O I
10.1021/ol5037369
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild and environmentally attractive dehalogenation of functionalized aryl halides has been developed using nanoparticles formed from PdCl2 in the presence of tetramethyldisiloxane (TMDS) on water. The active catalyst and reaction medium can be recycled. This method can also be applied to cascade reactions in a one-pot sequence.
引用
收藏
页码:1122 / 1125
页数:4
相关论文
共 28 条
[1]   METAL-HALOGEN INTERCHANGE BETWEEN TERT-BUTYLLITHIUM AND 1-IODO-5-HEXENES PROVIDES NO EVIDENCE FOR SINGLE-ELECTRON TRANSFER [J].
BAILEY, WF ;
PATRICIA, JJ ;
NURMI, TT ;
WANG, W .
TETRAHEDRON LETTERS, 1986, 27 (17) :1861-1864
[2]   1,1′-spirobiindane-7,7′-diol:: a novel, C2-symmetric chiral ligand [J].
Birman, VB ;
Rheingold, AL ;
Lam, KC .
TETRAHEDRON-ASYMMETRY, 1999, 10 (01) :125-131
[3]   PdCl2-catalyzed reduction of organic halides by triethylsilane [J].
Boukherroub, R ;
Chatgilialoglu, C ;
Manuel, G .
ORGANOMETALLICS, 1996, 15 (05) :1508-1510
[4]   Pd/C-catalyzed room-temperature hydrodehalogenation of aryl halides with hydrazine hydrochloride [J].
Cellier, PP ;
Spindler, JF ;
Taillefer, M ;
Cristau, HJ .
TETRAHEDRON LETTERS, 2003, 44 (38) :7191-7195
[5]   Room-Temperature Hydrodehalogenation of Halogenated Heteropentalenes with One or Two Heteroatoms [J].
Chelucci, Giorgio ;
Baldino, Salvatore ;
Ruiu, Andrea .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (21) :9921-9925
[6]  
Effenberger F, 2002, ANGEW CHEM INT EDIT, V41, P1699, DOI 10.1002/1521-3773(20020517)41:10<1699::AID-ANIE1699>3.0.CO
[7]  
2-N
[8]   Reduction of aryl halides by consecutive visible light-induced electron transfer processes [J].
Ghosh, Indrajit ;
Ghosh, Tamal ;
Bardagi, Javier I. ;
Koenig, Burkhard .
SCIENCE, 2014, 346 (6210) :725-728
[9]   Silane-based hydrogen storage materials for fuel cell application: Hydrogen release via methanolysis and regeneration by hydride reduction from organosilanes [J].
Han, Won-Sik ;
Kim, Tae-Jin ;
Kim, Sung-Kwan ;
Kim, Yongmin ;
Kim, Yeongcheon ;
Nam, Suk-Woo ;
Kang, Sang Ook .
INTERNATIONAL JOURNAL OF HYDROGEN ENERGY, 2011, 36 (19) :12305-12312
[10]   Dehalogenation of polychlorinated biphenyls and polybrominated diphenyl ethers using a hybrid bioinorganic catalyst [J].
Harrad, Stuart ;
Robson, Matthew ;
Hazrati, Sadegh ;
Baxter-Plant, Victoria S. ;
Deplanche, Kevin ;
Redwood, Mark D. ;
Macaskie, Lynne E. .
JOURNAL OF ENVIRONMENTAL MONITORING, 2007, 9 (04) :314-318