Application of copper(i) salt and fluoride promoted Stille coupling reactions in the synthesis of bioactive molecules

被引:27
作者
Lee, Victor [1 ]
机构
[1] Univ Oxford, Dept Chem, Chem Res Lab, 12 Mansfield Rd, Oxford OX1 3TA, England
关键词
RADICAL ALKYNE HYDROSTANNATION; FORMAL TOTAL-SYNTHESIS; ALDOL REACTIONS; EFFICIENT SYNTHESIS; ORGANOTIN COMPOUNDS; 9Z-RETINOIC ACID; TERMINAL ALKYNES; NATURAL-PRODUCT; ORGANIC HALIDES; ALDEHYDES;
D O I
10.1039/c9ob01602c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Stille coupling between organostannanes and organohalides is an effective catalytic method for organic synthesis. Despite the ample amount of published results in this area, finding the optimal conditions for this transformation is often not straightforward. It was observed that this reaction could be accelerated with improved efficiency by the addition of a Cu(i) salt and fluoride. This review summarises the application of this simple protocol in the synthesis of natural products, their analogues and other biologically active molecules, from 2004 to 2018.
引用
收藏
页码:9095 / 9123
页数:29
相关论文
共 88 条
[1]  
ABAS A, 1995, SYNLETT, P1264
[2]  
[Anonymous], 1992, ORGANIC REACTIONS, V50
[3]   REACTIONS OF ORGANIC HALIDES WITH R3MMR3 COMPOUNDS (M=SI,GE,SN) IN PRESENCE OF TETRAKIS(TRIARYLPHOSPHINE) PALLADIUM [J].
AZARIAN, D ;
DUA, SS ;
EABORN, C ;
WALTON, DRM .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1976, 117 (03) :C55-C57
[4]   Asymmetric Total Synthesis of (-)-(3R)-Inthomycin C [J].
Balcells, Sandra ;
Haughey, Maxwell B. ;
Walker, Johannes C. L. ;
Josa-Cullere, Laia ;
Towers, Christopher ;
Donohoe, Timothy J. .
ORGANIC LETTERS, 2018, 20 (12) :3583-3586
[5]   Biomimetic synthesis of elysiapyrones A and B [J].
Barbarow, JE ;
Miller, AK ;
Trauner, D .
ORGANIC LETTERS, 2005, 7 (14) :2901-2903
[6]   Total synthesis of (-)-SNF4435 C and (+)-SNF4435 D [J].
Beaudry, CM ;
Trauner, D .
ORGANIC LETTERS, 2005, 7 (20) :4475-4477
[8]   Total Synthesis of the Putative Structure of Nagelamide D [J].
Bhandari, Manojkumar R. ;
Sivappa, Rasapalli ;
Lovely, Carl J. .
ORGANIC LETTERS, 2009, 11 (07) :1535-1538
[9]   Synthesis of the Phenylpyridal Scaffold as a Helical Peptide Mimetic [J].
Bourne, Gregory T. ;
Kuster, Daniel J. ;
Marshall, Garland R. .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (28) :8439-8445
[10]   Efficient enantioselective additions of terminal alkynes and aldehydes under operationally convenient conditions [J].
Boyall, D ;
Frantz, DE ;
Carreira, EM .
ORGANIC LETTERS, 2002, 4 (15) :2605-2606