Palladium(II)-Catalyzed ortho Alkylation of Benzoic Acids with Alkyl Halides

被引:229
作者
Zhang, Yang-Hui [1 ]
Shi, Bing-Feng [1 ]
Yu, Jin-Quan [1 ]
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
基金
美国国家卫生研究院;
关键词
alkylation; benzoic acid; benzolactones; C-H activation; C-H ACTIVATION; PALLADIUM-CATALYZED ARYLATION; ARYL HALIDES; DIRECT FUNCTIONALIZATION; COUPLING REACTIONS; BOND ACTIVATION; DERIVATIVES; CLEAVAGE; HETEROCYCLES; TOSYLATES;
D O I
10.1002/anie.200902262
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Outsmarting the competition: In the PdII-catalyzed reaction of benzoates with alkyl halides, an aryl C-H bond is activated before the competitive alkylation of the carboxylate anion can takes place. The alkylation reaction was followed by an intramolecular lactonization to give broadly useful γ- and δ-benzolactones (see scheme). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:6097 / 6100
页数:4
相关论文
共 63 条
[51]   A CONVENIENT SYNTHESIS OF ACYCLIC CONJUGATED ENEDIYNES [J].
SHIBUYA, M ;
SAKAI, Y ;
NAOE, Y .
TETRAHEDRON LETTERS, 1995, 36 (06) :897-898
[52]   Intramolecular Pd-mediated processes of amino-tethered aryl halides and ketones:: Insight into the ketone α-arylation and carbonyl-addition dichotomy.: A new class of four-membered azapalladacycles [J].
Solé, D ;
Vallverdú, L ;
Solans, X ;
Font-Bardía, M ;
Bonjoch, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (06) :1587-1594
[53]   Catalytic C-H arylation of SEM-protected azoles with palladium complexes of NHCs and phosphines [J].
Touré, BB ;
Lane, BS ;
Sames, D .
ORGANIC LETTERS, 2006, 8 (10) :1979-1982
[54]   ORTHO-ALKYLATION OF ACETANILIDES USING ALKYL-HALIDES AND PALLADIUM ACETATE [J].
TREMONT, SJ ;
RAHMAN, HU .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (19) :5759-5760
[55]   Direct palladium-catalyzed alkenylation, benzylation and alkylation of ethyl oxazole-4-carboxylate with alkenyl-, benzyl- and alkyl halides [J].
Verrier, Cecile ;
Hoarau, Christophe ;
Marsais, Francis .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (04) :647-650
[56]   Palladium-catalyzed sp3 C-H activation of simple alkyl groups:: Direct preparation of indoline derivatives from N-alkyl-2-bromoanilines [J].
Watanabe, Toshiaki ;
Oishi, Shinya ;
Fujii, Nobutaka ;
Ohno, Hiroaki .
ORGANIC LETTERS, 2008, 10 (09) :1759-1762
[57]   Hypervalent iodine in synthesis XXXIV:: Palladium-catalyzed coupling reaction of o-hydroxyarylaldehydes with hypervalent iodonium salts via cleavage of the aldehyde C-H bond [J].
Xia, M ;
Chen, ZC .
SYNTHETIC COMMUNICATIONS, 2000, 30 (03) :531-536
[58]   Highly regloselective arylation of Sp3 C-H bonds catalyzed by palladium acetate [J].
Zaitsev, VG ;
Shabashov, D ;
Daugulis, O .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (38) :13154-13155
[59]   Consecutive vinylic to aryl to allylic palladium migration and multiple C-H activation processes [J].
Zhao, J ;
Campo, M ;
Larock, RC .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (12) :1873-1875
[60]  
Zhao J., 2005, ANGEW CHEM, V117, P1907