trans-bromo[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl][bis(tricyclohexylphosphine)]nickel(II)

Base Information

• Chemical Name: trans-bromo[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl][bis(tricyclohexylphosphine)]nickel(II)
• CAS No.: 447405-44-9
• Molecular Formula: C₄₈H₈₂BBrNiO₂P₂
• Molecular Weight: 902.53
• Mol file: 447405-44-9.mol

Synonyms:trans-bromo[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl][bis(tricyclohexylphosphine)]nickel(II)

Chemical Property of trans-bromo[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl][bis(tricyclohexylphosphine)]nickel(II)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-bromo[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl][bis(tricyclohexylphosphine)]nickel(II)

There total 6 articles about trans-bromo[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl][bis(tricyclohexylphosphine)]nickel(II) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.2%

bis(1,5-cyclooctadiene)nickel (0) (1295-35-8) + 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl trifluoromethanesulfonate (1437769-72-6) + lithium bromide (7550-35-8) + tricyclohexylphosphine (2622-14-2) → trans-bromo[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl][bis(tricyclohexylphosphine)]nickel(II) (447405-44-9)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.orglett.6b02831

Reference yield: 94.0%

[NiBr(o-C6H4B(pinacolate))(PPh3)2] (447405-43-8) + tricyclohexylphosphine (2622-14-2) → trans-bromo[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl][bis(tricyclohexylphosphine)]nickel(II) (447405-44-9)

Guidance literature:

In diethyl ether; the soln. in ether was stirred for 2 h at room temp. (N2); ppt. was filtered; elem. anal.;

DOI:10.1021/ja0264091

Reference yield:

(2-bromophenyl)boronic acid (244205-40-1) → trans-bromo[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl][bis(tricyclohexylphosphine)]nickel(II) (447405-44-9)

Guidance literature:

Multi-step reaction with 3 steps

1: pentane

2: Zn / tetrahydrofuran

3: diethyl ether

With Zn; In tetrahydrofuran; diethyl ether; pentane;

DOI:10.1021/ja0264091

upstream raw materials:

[NiBr(o-C₆H₄B(pinacolate))(PPh₃)2]

tricyclohexylphosphine

(2-bromophenyl)boronic acid

2-(2-bromophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Downstream raw materials:

[Ni(η2-C6H4)(P(C6H11)3)2]

cis-bromo[1,2-bis(dicyclohexylphosphino)ethane][2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]nickel(II)

[η²-benzyne][1,2-bis(dicyclohexylphosphino)ethane]nickel(0)