SO2 conversion to sulfones: development and mechanistic insights of a sulfonylative Hiyama cross-coupling

被引:21
作者
Adenot, Aurelien [1 ]
Char, Joelle [1 ]
von Wolff, Niklas [1 ]
Lefevre, Guillaume [1 ]
Anthore-Dalion, Lucile [1 ]
Cantat, Thibault [1 ]
机构
[1] Univ Paris Saclay, CNRS, CEA, NIMBE,CEA Saclay, F-91191 Gif Sur Yvette, France
基金
欧洲研究理事会;
关键词
SULFUR-DIOXIDE; REDUCTIVE ELIMINATION; ONE-POT; 3-COMPONENT; PALLADIUM; DABSO; COMPLEXES; LIGANDS;
D O I
10.1039/c9cc06858a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A Pd-catalyzed Hiyama cross-coupling reaction using SO2 is described. The use of silicon-based nucleophiles leads to the formation of allyl sulfones under mild conditions with a broad functional group tolerance. Control experiments coupled with DFT calculations shed light on the key steps of the reaction mechanism, revealing the crucial role of a transient sulfinate anion.
引用
收藏
页码:12924 / 12927
页数:4
相关论文
共 25 条
[1]  
Bouchez L, 2002, SYNTHESIS-STUTTGART, P225
[2]   Copper(I)-catalyzed sulfonylative Suzuki-Miyaura cross-coupling [J].
Chen, Yiding ;
Willis, Michael C. .
CHEMICAL SCIENCE, 2017, 8 (04) :3249-3253
[3]   DABSO-Based, Three-Component, One-Pot Sulfone Synthesis [J].
Deeming, Alex S. ;
Russell, Claire J. ;
Hennessy, Alan J. ;
Willis, Michael C. .
ORGANIC LETTERS, 2014, 16 (01) :150-153
[4]   KINETICS OF OXIDATIVE ADDITION OF ZEROVALENT PALLADIUM TO AROMATIC IODIDES [J].
FAUVARQUE, JF ;
PFLUGER, F ;
TROUPEL, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1981, 208 (03) :419-427
[5]   Organometallic chemistry of amidate complexes.: Accelerating effect of bidentate ligands on the reductive elimination of N-aryl amidates from palladium(II) [J].
Fujita, Ken-ichi ;
Yamashita, Makoto ;
Puschmann, Florian ;
Alvarez-Falcon, Miguel Martinez ;
Incarvito, Christopher D. ;
Hartwig, John F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (28) :9044-9045
[6]   Facile Ar-CF3 bond formation at Pd.: Strikingly different outcomes of reductive elimination from [(Ph3P)2Pd(CF3)Ph] and [(Xantphos)Pd(CF3)Ph] [J].
Grushin, Vladimir V. ;
Marshall, William J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12644-12645
[7]   CARBONYLATIVE COUPLING REACTION OF ORGANOFLUOROSILANES WITH ORGANIC HALIDES PROMOTED BY FLUORIDE-ION AND PALLADIUM CATALYST [J].
HATANAKA, Y ;
FUKUSHIMA, S ;
HIYAMA, T .
TETRAHEDRON, 1992, 48 (11) :2113-2126
[8]   ALPHA-SELECTIVE CROSS-COUPLING REACTION OF ALLYLTRIFLUOROSILANES - REMARKABLE LIGAND EFFECT ON THE REGIOCHEMISTRY [J].
HATANAKA, Y ;
GODA, K ;
HIYAMA, T .
TETRAHEDRON LETTERS, 1994, 35 (35) :6511-6514
[9]   PALLADIUM-CATALYZED CARBONYLATIVE COUPLING OF ARYLFLUOROSILANES WITH ARYL IODIDES - A CONVENIENT SYNTHESIS OF DIARYL KETONES [J].
HATANAKA, Y ;
HIYAMA, T .
CHEMISTRY LETTERS, 1989, (11) :2049-2052
[10]  
JULIA M, 1973, TETRAHEDRON LETT, P4833