Transition Metal-Catalyzed Migratory Tsuji-Trost Reaction

被引:4
作者
Chen, Xian-Xiao [1 ]
He, Zhi-Tao [1 ,2 ]
机构
[1] Univ Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, R China, Shanghai 200032, Peoples R China
[2] Univ Chinese Acad Sci, Hangzhou Inst Adv Study, Sch Chem & Mat Sci, Hangzhou 310024, Peoples R China
基金
中国国家自然科学基金;
关键词
Migratory Tsuji-Trost reaction; Leaving group migration; Olefin migration; Palladium catalyst; ALLYLIC SUBSTITUTION; HYDROALKYLATION; 1,3-DIENES; ALKYLATION; MECHANISM; CENTERS; DIENES; AMINES; AZIDES;
D O I
10.1002/cctc.202301073
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
Beyond the scope of classical Tsuji-Trost reaction, an alkene bearing a remote leaving group is not considered as a potential substrate for allylation. The concept of migratory Tsuji-Trost reaction focuses on the transformations with this type of substrates. Two pathways including olefin migration and leaving group migration to form typical allyl intermediate for following substitution have been explored to demonstrate the feasibility of this new concept. The development of migratory Tsuji-Trost reaction as a new reaction area via olefin migration or leaving group migration to generate critical pi-allyl Pd intermediate was summarized.image
引用
收藏
页数:6
相关论文
共 43 条
[1]   Enantioselective Construction of Quaternary Stereogenic Centers by the Addition of an Acyl Anion Equivalent to 1,3-Dienes [J].
Adamson, Nathan J. ;
Park, Sangjune ;
Zhou, Pengfei ;
Nguyen, Andrew L. ;
Malcolmson, Steven J. .
ORGANIC LETTERS, 2020, 22 (05) :2032-2037
[2]   Catalytic Enantio- and Regioselective Addition of Nucleophiles in the Intermolecular Hydrofunctionalization of 1,3-Dienes [J].
Adamson, Nathan J. ;
Malcolmson, Steven J. .
ACS CATALYSIS, 2020, 10 (02) :1060-1076
[3]   Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles [J].
Adamson, Nathan J. ;
Wilbur, Katherine C. E. ;
Malcolmson, Steven J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (08) :2761-2764
[4]   Enantioselective Intermolecular Addition of Aliphatic Amines to Acyclic Dienes with a Pd-PHOX Catalyst [J].
Adamson, Nathan J. ;
Hull, Ethan ;
Malcolmson, Steven J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (21) :7180-7183
[5]   Transition metal-catalyzed allylic substitution reactions with unactivated allylic substrates [J].
Butt, Nicholas A. ;
Zhang, Wanbin .
CHEMICAL SOCIETY REVIEWS, 2015, 44 (22) :7929-7967
[6]   Fluorescent Flippers: Small-Molecule Probes to Image Membrane Tension in Living Systems [J].
Chen, Xiao-Xiao ;
Bayard, Felix ;
Gonzalez-Sanchis, Nerea ;
Pamungkas, Khurnia Krisna Puji ;
Sakai, Naomi ;
Matile, Stefan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (20)
[7]   Palladium-catalyzed regio- and enantioselective migratory allylic C(sp3)-H functionalization [J].
Chen, Ye-Wei ;
Liu, Yang ;
Lu, Han-Yu ;
Lin, Guo-Qiang ;
He, Zhi-Tao .
NATURE COMMUNICATIONS, 2021, 12 (01)
[8]   Nickel-Catalyzed Isomerization/Allylic Cyanation of Alkenyl Alcohols [J].
Ding, Ying ;
Long, Jinguo ;
Sun, Feilong ;
Fang, Xianjie .
ORGANIC LETTERS, 2021, 23 (15) :6073-6078
[9]   A Modified Cationic Mechanism for PdCl2-Catalyzed Transformation of a Homoallylic Alcohol to an Allyl Ether [J].
Farshadfar, Kaveh ;
Chipman, Antony ;
Hosseini, Mandieh ;
Yates, Brian F. ;
Ariafard, Alireza .
ORGANOMETALLICS, 2019, 38 (15) :2953-2962
[10]   Pd-catalyzed enantioselective allylic substitution: New strategic options for the total synthesis of natural products [J].
Graening, T ;
Schmalz, HG .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (23) :2580-2584