Borylated Methylenephosphonium Salts: Precursors of Elusive Boryl(phosphino)carbenes

被引:32
作者
Lavigne, Florie [1 ,2 ]
Maerten, Eddy [1 ,2 ]
Alcaraz, Gilles [3 ]
Saffon-Merceron, Nathalie [4 ]
Acosta-Silva, Carles [5 ]
Branchadell, Vicenc [5 ]
Baceiredo, Antoine [1 ,2 ]
机构
[1] Univ Toulouse, UPS, F-31062 Toulouse, France
[2] Univ Toulouse, CNRS, LHFA, F-31062 Toulouse, France
[3] CNRS, LCC, UPR 8241, F-31077 Toulouse, France
[4] FR 2599, F-31062 Toulouse, France
[5] Univ Autonoma Barcelona, Dept Quim, E-08193 Barcelona, Spain
关键词
X-RAY CRYSTAL; CARBENES;
D O I
10.1021/ja103422b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthesis of a new family of boryl-substituted methylenephosphonium derivatives, the phosphorus analogues of iminium salts, has been developed. They were used in the preparation of the first stable boryl(phosphino)carbene, which has been fully characterized by NMR spectroscopy and X-ray crystallography. Density functional theory calculations indicate that these carbenes can be classified as push-pull carbenes with a relatively small singlet-triplet energy gap.
引用
收藏
页码:8864 / +
页数:4
相关论文
共 29 条
[1]   A STABLE CRYSTALLINE CARBENE [J].
ARDUENGO, AJ ;
HARLOW, RL ;
KLINE, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363
[2]   SYNTHESIS OF THE 1ST DISTILLABLE ALPHA-BORANYLDIAZOMETHANE - DIRECT EVIDENCE OF LITHIOBORANYLDIAZOMETHANE-LITHIOBORANYLISODIAZO-METHANE [(BCNN-,LI+)-(BNNC-,LI+)] REARRANGEMENT [J].
ARTHUR, MP ;
BACEIREDO, A ;
BERTRAND, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (15) :5856-5857
[3]   Stable carbenes [J].
Bourissou, D ;
Guerret, O ;
Gabbaï, FP ;
Bertrand, G .
CHEMICAL REVIEWS, 2000, 100 (01) :39-91
[4]   Stable versions of transient push-pull carbenes: Extending lifetimes from nanoseconds to weeks [J].
Buron, C ;
Gornitzka, H ;
Romanenko, V ;
Bertrand, G .
SCIENCE, 2000, 288 (5467) :834-836
[5]   Stable non-N-heterocyclic carbenes (non-NHC): recent progress [J].
Canac, Y ;
Soleilhavoup, M ;
Conejero, S ;
Bertrand, G .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (24) :3857-3865
[6]   Structural changes accompanying the stepwise population of a B-C π bond [J].
Chiu, Ching-Wen ;
Gabbaie, Francois P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (36) :6878-6881
[7]   BORON-ACTIVATION OF ACETYLENES TO NUCLEOPHILIC-ADDITION REACTIONS [J].
COOKE, MP .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :2930-2931
[8]  
Despagnet E, 2002, ANGEW CHEM INT EDIT, V41, P2835, DOI 10.1002/1521-3773(20020802)41:15<2835::AID-ANIE2835>3.0.CO
[9]  
2-8
[10]   (Aryl)(phosphanyl)carbene: Ground- and excited-state reactions [J].
Despagnet-Ayoub, E ;
Gornitzka, H ;
Bourissou, D ;
Bertrand, G .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (11) :2039-2042