Enantioselective Synthesis of Biaryl Atropisomers via Pd/Norbornene-Catalyzed Three-Component Cross-Couplings

被引:103
作者
Ding, Linlin [1 ]
Sui, Xianwei [1 ]
Gu, Zhenhua [1 ]
机构
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Ctr Excellence Mol Synth, Dept Chem, 96 Jinzhai Rd, Hefei 230026, Anhui, Peoples R China
关键词
cross-coupling palladium; norbornene; atropisomer; asymmetric catalysis; AXIALLY CHIRAL BIARYLS; SUZUKI-MIYAURA REACTION; C-H FUNCTIONALIZATION; ATROPOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; NATURAL-PRODUCTS; ARYL IODIDES; LIGANDS; COMPLEXES;
D O I
10.1021/acscatal.8b01037
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Three-component cross-coupling cocatalyzed by palladium and norbornene is reported for the synthesis of biaryl atropisomers. This domino reaction gave optimal yield and enantioselectivity with a P,C-type ligand bearing axial chirality and P chiral center. The process showed advantages over traditional cross-coupling because of its step economy and its compatibility with readily available ortho-substituted aryl halides, which could, therefore, be used instead of continuously trisubstituted aryl halides.
引用
收藏
页码:5630 / 5635
页数:11
相关论文
共 75 条
[1]   Stronger Bronsted Acids: Recent Progress [J].
Akiyama, Takahiko ;
Mori, Keiji .
CHEMICAL REVIEWS, 2015, 115 (17) :9277-9306
[2]   Synthesis of New Axially Chiral Iodoarenes [J].
Bekkaye, Mathieu ;
Masson, Geraldine .
SYNTHESIS-STUTTGART, 2016, 48 (02) :302-312
[3]   Chiral PEPPSI Complexes: Synthesis, Characterization, and Application in Asymmetric Suzuki-Miyaura Coupling Reactions [J].
Benhamou, Laure ;
Besnard, Celine ;
Kuendig, E. Peter .
ORGANOMETALLICS, 2014, 33 (01) :260-266
[4]   C2-Symmetric Bis-Hydrazones as Ligands in the Asymmetric Suzuki-Miyaura Cross-Coupling [J].
Bermejo, Antonio ;
Ros, Abel ;
Fernandez, Rosario ;
Lassaletta, Jose M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (47) :15798-+
[5]   Modified BINAP: The how and the why [J].
Berthod, M ;
Mignani, G ;
Woodward, G ;
Lemaire, M .
CHEMICAL REVIEWS, 2005, 105 (05) :1801-1836
[6]   Asymmetric Synthesis of QUINAP via Dynamic Kinetic Resolution [J].
Bhat, Vikram ;
Wang, Su ;
Stoltz, Brian M. ;
Virgil, Scott C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (45) :16829-16832
[7]   Stereoselective total synthesis of axially chiral natural products via biaryl lactones [J].
Bringmann, G ;
Menche, D .
ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (08) :615-624
[8]   Atroposelective synthesis of axially chiral biaryl compounds [J].
Bringmann, G ;
Mortimer, AJP ;
Keller, PA ;
Gresser, MJ ;
Garner, J ;
Breuning, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) :5384-5427
[9]   Catalytic multistep reactions via palladacycles [J].
Catellani, M .
SYNLETT, 2003, (03) :298-313
[10]   A complex catalytic cycle leading to a regioselective synthesis of o,o'-disubstituted vinylarenes [J].
Catellani, M ;
Frignani, F ;
Rangoni, A .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (1-2) :119-122