Iridium-catalyzed alkenyl C-H allylation using conjugated dienes

被引:37
作者
Xu, Liangyao [1 ]
Meng, Keke [1 ]
Zhang, Jian [1 ]
Sun, Yaling [1 ]
Lu, Xiunan [1 ]
Li, Tingyan [1 ]
Jiang, Yan [1 ]
Zhong, Guofu [1 ]
机构
[1] Hangzhou Normal Univ, Coll Mat Chem & Chem Engn, Hangzhou 311121, Zhejiang, Peoples R China
基金
中国国家自然科学基金;
关键词
ELECTRON-DEFICIENT ALKENES; ALLYLIC CARBONATES; FACILE SYNTHESIS; HYDROARYLATION; ACCESS; ACTIVATION; OLEFINATION; ALKYLATION; 1,3-DIENES; EFFICIENT;
D O I
10.1039/c9cc04419a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An iridium-catalyzed C-H allylation of acrylamides with conjugated dienes was developed, using NH-Ts amide as the directing group. The ligand-and additive-free protocol provided a convenient and atom economic synthesis of branched 1,4-diene skeletons, enabling the tolerance of a wide scope of functionalities such as OMe, F, Cl, Br and CF3. The utility of this protocol is also demonstrated by a preparative scale, as well as C-H functionalization of artemisic amide. Furthermore, NH-Ts amide was efficiently removed by methylation and hydrolysis procedures to provide 1,4-dienoic acid.
引用
收藏
页码:9757 / 9760
页数:4
相关论文
共 77 条
[1]   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
[2]   The Baylis-Hillman reaction: One-pot facile synthesis of 2,4-functionalized 1,4-pentadienes [J].
Basavaiah, D ;
Sharada, DS ;
Kumaragurubaran, N ;
Reddy, RM .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :7135-7137
[3]   Baylis-Hillman chemistry: a novel synthesis of functionalized 1,4-pentadienes [J].
Basavaiah, D ;
Kumaragurubaran, N ;
Sharada, DS .
TETRAHEDRON LETTERS, 2001, 42 (01) :85-87
[4]   Acylsilanes in Iridium-Catalyzed Directed Amidation Reactions and Formation of Heterocycles via Siloxycarbenes [J].
Becker, Peter ;
Pirwerdjan, Ramona ;
Bolm, Carsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (51) :15493-15496
[5]   RhIII-Catalyzed Oxidative Olefination of Vinylic C-H Bonds: Efficient and Selective Access to Di-unsaturated α-Amino Acid Derivatives and Other Linear 1,3-Butadienes [J].
Besset, Tatiana ;
Kuhl, Nadine ;
Patureau, Frederic W. ;
Glorius, Frank .
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (26) :7167-7171
[6]   Iridium-Catalyzed Asymmetric Allylic Substitution Reactions [J].
Cheng, Qiang ;
Tu, Hang-Fei ;
Zheng, Chao ;
Qu, Jian-Ping ;
Helmchen, Guenter ;
You, Shu-Li .
CHEMICAL REVIEWS, 2019, 119 (03) :1855-1969
[7]   Stereoselective Total Synthesis of Bioactive Marine Natural Product Biselyngbyolide B [J].
Das, Sayantan ;
Paul, Debobrata ;
Goswami, Rajib Kumar .
ORGANIC LETTERS, 2016, 18 (08) :1908-1911
[8]   Tandem inter [4+2] intra [3+2] cycloadditions of nitroalkenes .15. The bridged mode (alpha-tether) [J].
Denmark, SE ;
Guagnano, V ;
Dixon, JA ;
Stolle, A .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) :4610-4628
[9]   Construction of (Z,Z) skipped 1,4-dienes.: Application to the synthesis of polyunsaturated fatty acids and derivatives [J].
Durand, S ;
Parrain, JL ;
Santelli, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (03) :253-273
[10]   Iridium-Catalyzed Regio- and Enantioselective Hydroarylation of Alkenyl Ethers by Olefin Isomerization [J].
Ebe, Yusuke ;
Onoda, Mitsuki ;
Nishimura, Takahiro ;
Yorimitsu, Hideki .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (20) :5607-5611