C-H Activation for the Construction of C-B Bonds

被引:2313
作者
Mkhalid, Ibraheem A. I. [1 ,2 ]
Barnard, Jonathan H. [1 ]
Marder, Todd B. [1 ]
Murphy, Jaclyn M. [3 ,4 ]
Hartwig, John F. [4 ]
机构
[1] Univ Durham, Dept Chem, Durham DH1 3LE, England
[2] King Abdulaziz Univ, Dept Chem, Jeddah 21413, Saudi Arabia
[3] Yale Univ, Dept Chem, New Haven, CT USA
[4] Univ Illinois, Dept Chem, Sci Lab, Urbana, IL 61801 USA
关键词
TRANSITION-METAL-BORYL; CATALYZED DEHYDROGENATIVE BORYLATION; OLEFIN CROSS-METATHESIS; ROOM-TEMPERATURE REACTIONS; CAT EQUALS 1,2-O2C6H4; CARBON-HYDROGEN-BONDS; CYCLIC VINYL ETHERS; ONE-POT SYNTHESIS; ARYLBORONIC ACIDS; COUPLING REACTION;
D O I
10.1021/cr900206p
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A number of studies were conducted to demonstrate C-H activation for the construction of C-B bonds. Investigations revealed that the conversion of C-H bonds to C-B bonds was both thermodynamically and kinetically favorable. The reaction at a primary C-H bond of methane or a higher alkene B 2(OR)4 formed an alkylboronate ester R' -B(OR)2 and the accompanying borane H-B(OR2. The ester and the borane were formed on the basis of calculated bond energies for methylboronates and dioaborolanes. The rates of key steps along the reaction pathway for the conversion of a C-H bond in an alkane or arene to the C-B bond in an alkyl or arylboronate ester were favorable. These studies also highlighted the accessible barriers for C-H bond cleavage and B-C bond formation during the borylation of alkanes and arenes.
引用
收藏
页码:890 / 931
页数:42
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