Iridium-Catalyzed Enantioselective Hydroarylation of Alkenes through C-H bond Activation: Experiment and Computation

被引:25
作者
Shinde, Valmik S. [1 ]
Mane, Manoj V. [1 ]
Cavallo, Luigi [1 ]
Rueping, Magnus [1 ]
机构
[1] King Abdullah Univ Sci & Technol, KAUST Catalysis Ctr, Thuwal 239556900, Saudi Arabia
关键词
asymmetric catalysis; C-H activation; hydroarylation; iridium; quniox P*; PINACOL MACROCYCLIZATION CASCADE; AROMATIC IMINES; INTRAMOLECULAR HYDROARYLATION; COUPLING REACTIONS; HYDROGEN-BONDS; DIAZONAMIDE-A; CYCLIZATION; CONSTRUCTION; FUNCTIONALIZATION; ALKYLATION;
D O I
10.1002/chem.202001793
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new catalytic enantioselective hydroarylation of unactivated olefins is developed that provides rapid access to functionalized chiral dihydrobenzofurans with good yields and excellent enantioselectivities. Simple aromatic ketones or amides act as a directing group allowing the regioselective reaction at the more hinderedorthoposition. Tertiary benzylic stereocenters are obtained directly under mild reaction conditions and with complete atom economy from readily available starting materials.
引用
收藏
页码:8308 / 8313
页数:6
相关论文
共 50 条
[31]   Iridium-Catalyzed α-Selective Arylation of Styrenes by Dual C-H Functionalization [J].
Cooper, Phillippa ;
Crisenza, Giacomo E. M. ;
Feron, Lyman J. ;
Bower, John F. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (43) :14198-14202
[32]   Iridium-Catalyzed Branch-Selective and Enantioselective Hydroalkenylation of α-Olefins through C-H Cleavage of Enamides [J].
Sun, Xin ;
Lin, En-Ze ;
Li, Bi-Jie .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (38) :17351-17358
[33]   Iridium-catalyzed borylation of arenes and heteroarenes via C-H activation [J].
Ishiyama, Tatsuo ;
Miyaura, Norio .
PURE AND APPLIED CHEMISTRY, 2006, 78 (07) :1369-1375
[34]   Development of a Tunable Chiral Pyridine Ligand Unit for Enantioselective Iridium-Catalyzed C-H Borylation [J].
Song, Peidong ;
Hu, Linlin ;
Yu, Tao ;
Jiao, Jiao ;
He, Yangqing ;
Xu, Liang ;
Li, Pengfei .
ACS CATALYSIS, 2021, 11 (12) :7339-7349
[35]   Chemoselectivity in Catalytic C-C and C-H Bond Activation: Controlling Intermolecular Carboacylation and Hydroarylation of Alkenes [J].
Wentzel, Michael T. ;
Reddy, Venkata Jaganmohan ;
Hyster, Todd K. ;
Douglas, Christopher J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (33) :6121-6123
[36]   Iridium-Catalyzed Remote Site-Switchable Hydroarylation of Alkenes Controlled by Ligands [J].
Li, Fei ;
Luo, Yicong ;
Ren, Jinbao ;
Yuan, Qianjia ;
Yan, Deyue ;
Zhang, Wanbin .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (41)
[37]   Iridium-Catalyzed C-H Activation and Deuteration of Primary Sulfonamides: An Experimental and Computational Study [J].
Kerr, William J. ;
Reid, Marc ;
Tuttle, Tell .
ACS CATALYSIS, 2015, 5 (01) :402-410
[38]   Iridium-Catalyzed Electrooxidative C-H Activation by Chemoselective Redox-Catalyst Cooperation [J].
Qiu, Youai ;
Stangier, Maximilian ;
Meyer, Tjark H. ;
Oliveira, Joao C. A. ;
Ackermann, Lutz .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (43) :14179-14183
[39]   Transformation of tert-Butyl Amide Directing Groups to Nitriles in Iridium-Catalyzed C-H Bond Functionalizations [J].
Kim, Dopil ;
Yoo, Haneul ;
Park, Myung Hwan ;
Kim, Youngjo ;
Chuang, Gary Jing ;
Yoo, Kwangho ;
Kim, Dongwook ;
Kim, Hyun Jin ;
Kim, Min .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (12) :3411-3420
[40]   Iridium-Catalyzed Reactions of Trifluoromethylated Compounds with Alkenes: A Csp3-H Bond Activation α to the Trifluoromethyl Group [J].
Guo, Yong ;
Zhao, Xiaming ;
Zhang, Dazhi ;
Murahashi, Shun-Ichi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (11) :2047-2049