Rhodium(III)‐Catalyzed Oxidative Olefination of Picolinamides: Convenient Synthesis of 3‐Alkenylpicolinamides

Advanced Synthesis and Catalysis - Tập 356 Số 5 - Trang 1038-1046 - 2014
Jun Zhou1, Bo Li1, Zhenchao Qian1, Bing‐Feng Shi1,2
1Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China, Fax: (+86)‐571‐8795‐1895, phone: (+86)‐571‐8795‐1352
2State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, People's Republic of China

Tóm tắt

AbstractA rhodium(III)‐catalyzed selective olefination of picolinamide derivatives has been developed. The reaction shows high regioselectivity, low catalyst loading (0.5 mol%), high yield and good functional group tolerance, providing a convenient strategy for the synthesis of 3‐alkenylpicolinamides.magnified image

Từ khóa


Tài liệu tham khảo

For selected reviews see:

10.1039/b602413k

10.1039/b706241a

10.1021/cr200251d

10.1002/chem.201001100

 

10.1038/nature11680

10.1021/ja1066459

10.1055/s-0030-1260212

For selected recent examples of arylation and alkylation of pyridines see:

10.1039/c3sc50348h

10.1021/ja209510q

10.1021/ja111670s

10.1021/ja109383e

10.1021/ja909807f

10.1002/ange.200906104

10.1002/anie.200906104

10.1021/ja9053509

10.1021/ja8059396

10.1021/ja710073n

10.1021/ja056800x

10.1021/ja3113752

10.1039/C0SC00419G

10.1021/ja106514b

10.1021/ja070388z

For selected recent alkenylation of pyridines see:

10.1021/ja2021075

10.1002/ange.200703758

10.1002/anie.200703758

10.1021/ja710766j

10.1021/ja1061246

10.1021/ja8026295

10.1002/ange.200906020

10.1002/anie.200906020

10.1021/ja308205d

 

10.1016/S0040-4039(00)90648-8

10.1126/science.287.5460.1992

10.1021/ja01053a047

For selected reviews see:

10.1016/j.tet.2008.01.052

10.1002/ange.200806273

10.1002/anie.200806273

10.1016/j.tet.2012.05.040

10.1021/cr100280d

10.1021/cr900184e

10.1002/ange.201203269

10.1002/anie.201203269

10.1039/c1cs15082k

10.1039/c1cs15013h

10.1039/C2SC21524A

For selected examples see:

10.1021/ol070406h

10.1021/jo901077r

10.1021/ja103834b

10.1002/ange.201006222

10.1002/anie.201006222

10.1021/ja109676d

10.1021/ol102890k

10.1021/ol1022596

10.1002/ange.201207204

10.1002/anie.201207204

10.1021/ol201140q

10.1021/ol200600p

10.1039/C2CC16963K

10.1002/ange.201203230

10.1002/anie.201203230

 

10.1039/c2cs15281a

Patureau F., 2012, Aldrichimica Acta, 45, 31

10.1002/asia.201200035

10.1002/chem.201001363

10.1021/cr900005n

For isolated examples see:

10.1021/jo200339w

10.1039/C1CC15248C

10.1002/ange.201201273

10.1002/anie.201201273

10.1021/ol400307d

10.1021/jo201266u

10.1039/c2ob25773d

10.1021/ol401540k

2–5 mol% Rh(III) catalyst were used previously see refs.[10 11]

 

Rh(III)‐catalyzed olefination of benzamides has been reported see ref.[8d]For C‐2 olefinaton of indoles withN‐benzoyl orN‐dimethylcarbamoyl directing groups see:

10.1039/c3cc44787a

10.1002/chem.201301987

10.1021/ol4011486

The olefinated product4fhas been prepared on the gram scale with 0.5 mol% [Cp*RhCl2]2in 87% yield.

10.1021/ja405140f