Divergent Palladium‐Catalyzed Cross‐Coupling of Nitropyrazoles with Terminal Alkynes

European Journal of Organic Chemistry - Tập 2018 Số 20-21 - Trang 2645-2650 - 2018
Hyeri Ha1, Chang-Hoon Shin1, Seri Bae1, Jung Min Joo1
1Department of Chemistry and Chemistry Institute of Functional Materials, Pusan National University, 46241 Busan, Republic of Korea

Tóm tắt

Facile homo‐coupling of terminal alkynes, which generates conjugated diynes, is an undesired pathway in the development of transition‐metal‐catalyzed oxidative C–H functionalization of (hetero)arenes with terminal alkynes. By incorporating this process into a catalytic cycle, we achieved regio‐ and stereoselective hydroarylation of nitropyrazoles with the resulting 1,3‐diynes. A simple change in the stoichiometry and oxidant allowed direct C–H alkynylation of nitropyrazoles, producing the corresponding alkynyl pyrazoles.

Từ khóa


Tài liệu tham khảo

10.1021/acs.chemrev.5b00514

10.1021/cr400133p

10.1002/9783527677894

10.1039/C5CS00892A

10.1016/j.tetlet.2014.03.022

10.1002/anie.200906755

10.1002/ange.200906755

10.1002/ejoc.201000928

10.1021/cr100280d

10.1039/c1cs15082k

10.1002/anie.201203269

10.1002/ange.201203269

10.1021/cr500431s

10.1021/ol100699g

10.1039/c0cc00014k

10.1021/jo3008385

10.1021/ja910461e

10.1021/ol200154s

10.1002/anie.201210013

10.1002/ange.201210013

10.1002/ejoc.200801054

10.1021/acs.chemrev.6b00567

10.1021/cr9903353

10.1021/jo7020554

10.1002/ejoc.201500417

10.1039/C5OB02045J

10.1002/anie.201403782

10.1002/ange.201403782

10.1021/ol5030794

10.1002/chem.201405903

10.1021/acs.joc.7b01867

10.1021/acs.orglett.7b02119

10.1021/jo501460h

10.1021/acs.orglett.6b03310

Yet L., 2008, Comprehensive Heterocyclic Chemistry, 1

10.1016/j.ejmech.2016.04.077

10.1021/jm3012239

10.1021/jo4025418

10.5012/bkcs.2014.35.10.3009

10.1021/jo5025317

10.1002/ajoc.201500388

10.1021/acs.joc.5b02398

10.1021/acs.joc.7b00550

10.1002/0471224480

10.1021/jacs.7b03159

10.1002/anie.201706982

10.1002/ange.201706982

10.1016/j.catcom.2013.07.019

10.1039/c2gc16539b

10.1021/ol200251x

10.1021/acscatal.7b01915

10.1039/C7OB01918A

10.1021/acs.orglett.6b01934

CCDC1818994 (for2a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge fromThe Cambridge Crystallographic Data Centre.

10.1021/ja2069246

10.1021/jacs.7b05436

10.1039/b602151b

Thông tin
Thông tin xuất bản

European Journal of Organic Chemistry

Tập 2018 Số 20-21

2645-2650

Thông tin tác giả