The Phenanthrolines for Copper-catalized Suzuki-Miyaura Cross-coupling Reaction

    Suzuki−Miyaura cross-couplings (SMC) are powerful tools to construct carbon-carbon bond. First-row transition metals catalyzed C(sp2)−C(sp3) couplings has been proved to be more successful due to the low propensity of β-hydride elimination.
      “A general Copper catalytic system for Suzuki-Miyaura cross-coupling of unactivated secondary and primary alkyl halides with arylborons” (J. Am. Chem. Soc. 2023, 145, 51, 28146–28155 https://doi.org/10.1021/jacs.3c10628) was reported.

      A highly efficient and operationally simple copper catalytic system for the couplings of arylborons with unactivated secondary and primary alkyl halides including iodides, bromides, and even inert chlorides under relatively mild conditions are presented. In the catalytic procedure, series of N-containing bidentate ligands were screened, shown as below. Bathophenanthroline CAS:1662-01-7 was approved to be the best ligand under the given conditions.

The current system is broad in scope of both coupling partners tolerating various functionalities, steric reagents, and complex molecules. Notably, the procedure is convenient to operate in air, allowing for the practicality of this method. Thus, the system would be served as a mild and general approach for the C(sp2)−C(sp3) Suzuki−Miyaura couplings. 

      About the phenanthroline derived symmetric/unsymmetric substituted analogues, UCHEM is one of main suppliers on the world. The following list are available from warehouse. Some products are available in kilograms, and several of them are supplying commercially.

1,10-phenanthrollne monohydrate CAS:5144-89-8

1,10-phenanthroline CAS:66-71-7

1,10-Phenanthroline monohydrochloride monohydrate CAS:3829-86-5

2,9-Dimethyl-1,10-phenanthroline CAS:484-11-7

2,9-Dimethyl-1,10-phenanthroline Hemihydrate CAS:34302-69-7

1,10-Phenanthroline-2,9-dicarbaldehyde CAS: 57709-62-3

1,10-phenanthroline-2,9-dicarboxylic acid CAS:57709-61-2

2,9-Dichloro-1,10-phenanthroline CAS:29176-55-4

2,9-Dibromo-1,10-phenanthroline CAS:39069-02-8

2,9-Diphenyl-1,10-phenanthroline CAS:25677-69-4

4,4'-(1,10-phenanthroline-2,9-diyl)dianiline CAS:861659-70-3

4,4'-(1,10-Phenanthroline-2,9-diyl)diphenol CAS:88498-43-5

2,2'-(1,10-phenanthroline-2,9-diyl)diphenol CAS:192631-69-9

2-Bromo-9-phenyl-1,10-phenanthroline CAS:2042493-16-1

2-Chloro-9-phenyl-1,10-phenanthroline CAS:1937210-90-6

2-Methyl-1,10-phenanthroline CAS:3002-77-5

1,10-Phenanthroline-2-carboxaldehyde CAS:33795-37-8

1,10-Phenanthroline-2-carboxylic acid CAS:1891-17-4

2-chloro-1,10-phenanthroline CAS:7089-68-1

2-Bromo-1,10-phenanthroline CAS:22426-14-8

1,10-Phenanthroline-2-carbonitrile CAS:1082-19-5

2-Phenyl-1,10-phenanthroline CAS:109559-47-9

2-(4-Bromophenyl)-1,10-phenanthroline CAS:149054-39-7

3,8-Dibromo-1,10-phenanthroline CAS:100125-12-0

3,8-Diethynyl-1,10-phenanthroline CAS:640297-84-3

3,8-Bis[(trimethylsilyl)ethynyl]-1,10-phenanthroline CAS:320573-10-2

4-Methyl-1,10-phenanthroline CAS:31301-28-7

1,10-Phenanthroline-4-carboxaldehyde CAS:31301-30-1

1,10-Phenanthroline-4-carboxylic acid CAS:31301-27-6

1,10-Phenanthrolin-4-ol CAS:23443-31-4

4-Bromo-1,10-phenanthroline CAS:7089-67-0

4-Chloro-1,10-phenanthroline CAS:1891-14-1

4-(4-Bromophenyl)-1,10-phenanthroline CAS:97802-07-8

4,7-Diphenyl-1,10-phenanthroline CAS:1662-01-7

4,7-Bis(4-bromophenyl)-1,10-phenanthroline CAS:97802-08-9

4,7-Dimethyl-1,10-phenanthroline CAS:3248-05-3

1,10-Phenanthroline-4,7-dicarboaldehyde CAS:130897-87-9

1,10-Phenanthroline-4,7-dicarboxylic acid CAS:31301-31-2

4,7-dihydroxy-1,10-phenanthroline CAS:3922-40-5

1,10-Dihydro-1,10-phenanthroline-4,7-dione CAS:87330-27-6

4,7-Dichloro-1,10-phenanthroline CAS:5394-23-0

4,7-dibromo-1,10-phenanthroline CAS:156492-30-7

4,7-Dimethoxy-1,10-phenanthroline CAS:92149-07-0

5-Methyl-1,10-phenanthroline CAS:3002-78-6

1,10-Phenanthroline-5-carboxaldehyde CAS:91804-75-0

1,10-Phenanthroline-5-carboxylic acid CAS:630067-06-0

5-Chloro-1,10-phenanthroline CAS:4199-89-7

5-Bromo-1,10-phenanthroline CAS:40000-20-2

5-Bromo-1,10-phenanthroline monohydrate CAS:855360-86-0

5-Nitro-1,10-phenanthroline CAS:4199-88-6

5-Amino-1,10-phenanthroline CAS:54258-41-2

1,10-Phenanthroline-5,6-dione CAS:27318-90-7

5,6-diamino-1,10-phenanthroline CAS:168646-54-6

5,6-Dimethyl-1,10-phenanthroline CAS:3002-81-1

2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline CAS:4733-39-5

3,4,7,8-Tetramethyl-1,10-phenanthroline CAS:1660-93-1

5,5'-Bi-1,10-phenanthroline CAS:96761-79-4

1,3-Bis(9-phenyl-1,10-phenanthrolin-2-yl)benzene CAS:721969-94-4