Photocatalyzed Csp3-Csp3 cross-dehydrogenative coupling of N-Boc-tetrahydroisoquinolines with α,β-unsaturated ketones

被引:5
作者
Ao, Na-Ri-Mei [1 ]
Zhu, Xue-Qing [1 ]
Zhao, Chun-Xin [1 ]
Gao, Ya-Ru [1 ]
Wang, Yong-Qiang [1 ]
机构
[1] Northwest Univ, Coll Chem & Mat Sci, Natl Demonstrat Ctr Expt Chem Educ, Key Lab Synthet & Nat Funct Mol Chem,Minist Educ, Xian 710069, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1039/d1ob00527h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel photocatalyzed cross-dehydrogenative coupling reaction of N-Boc-tetrahydroisoquinolines with alpha,beta-unsaturated ketones has been developed. This research provides an easy access to a variety of C1-substituted tetrahydroisoquinolines, which can be further transformed into benzo[a]-quinolizine-2-ones, the skeletons of natural products with a wide range of biological activities. The load of the photocatalyst is low and the oxidant is inexpensive and less toxic.
引用
收藏
页码:4752 / 4759
页数:8
相关论文
共 45 条
[1]   CDC Reactions of N-Aryl Tetrahydroisoquinolines Using Catalytic Amounts of DDQ: C-H Activation under Aerobic Conditions [J].
Alagiri, Kaliyamoorthy ;
Devadig, Pradeep ;
Prabhu, Kandikere R. .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (17) :5160-5164
[2]   Enantioselective copper-catalyzed conjugate addition and allylic substitution reactions [J].
Alexakis, A. ;
Backvall, J. E. ;
Krause, N. ;
Pamies, O. ;
Dieguez, M. .
CHEMICAL REVIEWS, 2008, 108 (08) :2796-2823
[3]   Recent advances in the Baylis-Hillman reaction and applications [J].
Basavaiah, D ;
Rao, AJ ;
Satyanarayana, T .
CHEMICAL REVIEWS, 2003, 103 (03) :811-891
[4]   The Baylis-Hillman reaction: a novel concept for creativity in chemistry [J].
Basavaiah, Deevi ;
Veeraraghavaiah, Gorre .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (01) :68-78
[5]   Recent Contributions from the Baylis-Hillman Reaction to Organic Chemistry [J].
Basavaiah, Deevi ;
Reddy, Bhavanam Sekhara ;
Badsara, Satpal Singh .
CHEMICAL REVIEWS, 2010, 110 (09) :5447-5674
[6]  
Bergonzini G, 2014, CHEM SCI, V5, P112, DOI [10.1039/C3SC52265B, 10.1039/c3sc52265b]
[7]   A metal-free cross-dehydrogenative coupling of N-carbamoyl tetrahydroisoquinoline by sodium persulfate [J].
Chen, Wenfang ;
Zheng, Hongbo ;
Pan, Xinhui ;
Xie, Zhiyu ;
Zan, Xin ;
Sun, Bin ;
Liu, Lei ;
Lou, Hongxiang .
TETRAHEDRON LETTERS, 2014, 55 (17) :2879-2882
[8]   Highly efficient metal-free cross-coupling by C-H activation between allylic and active methylenic compounds promoted by DDQ [J].
Cheng, Dongping ;
Bao, Weiliang .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (09) :1263-1266
[9]   Visible-Light Photoredox Catalysis: Aza-Henry Reactions via C-H Functionalization [J].
Condie, Allison G. ;
Gonzalez-Gomez, Jose C. ;
Stephenson, Corey R. J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) :1464-+
[10]   Fifty years of alkaloid biosynthesis in Phytochemistry [J].
Cordell, Geoffrey A. .
PHYTOCHEMISTRY, 2013, 91 :29-51