Oxidative homo-coupling reactions of aryl boronic acids using a porous copper metal-organic framework as a highly efficient heterogeneous catalyst
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07C-253/30
C07C-201/12
C07C-001/32
C07C-017/263
C07C-209/68
출원번호
US-0387598
(2010-07-27)
등록번호
US-9045387
(2015-06-02)
국제출원번호
PCT/US2010/043373
(2010-07-27)
§371/§102 date
20120127
(20120127)
국제공개번호
WO2011/014503
(2011-02-03)
발명자
/ 주소
Yaghi, Omar M.
Czaja, Alexander U.
Wang, Bo
Lu, Zheng
출원인 / 주소
The Regents of the University of California
대리인 / 주소
Baker, Jr., Joseph R.
인용정보
피인용 횟수 :
0인용 특허 :
29
초록
The disclosure provides methods for the use of open metal frameworks to catalyze coupling reactions.
대표청구항▼
1. A method to connect aryls by homocoupling comprising contacting a porous metal organic framework (MOF) or a porous metal organic polyhedral (MOP) with boronic acid substituted aryls wherein the MOF or MOP catalyze the synthesis of a biaryl through a homo-coupling reaction, wherein the MOF or MOP
1. A method to connect aryls by homocoupling comprising contacting a porous metal organic framework (MOF) or a porous metal organic polyhedral (MOP) with boronic acid substituted aryls wherein the MOF or MOP catalyze the synthesis of a biaryl through a homo-coupling reaction, wherein the MOF or MOP comprises a plurality of linking moieties that have a substructure selected from the group consisting of (C1-C20)alkyl, (C3C20)cycloalky, aryl, (C1-C20)alkylamine, arylamine, and heterocycle; and wherein the substructure has one or more covalently attached CO2H linking clusters that undergo condensation with a copper metal and wherein the MOF or the MOP comprise open copper centers that are mono-dispersed throughout the pores. 2. The method of claim 1, wherein the method further comprises cupric acetate. 3. The method of claim 1, wherein the method further comprises a solvent. 4. The method of claim 1, wherein the method further comprises a base. 5. The method of claim 4, wherein the copper center of the MOF or the MOP forms a coordinate bond with the base. 6. The method of claim 1, wherein the method further comprises an oxidant. 7. The method of claim 6, wherein the one or more oxidant is air. 8. The method of claim 1, wherein the method is performed at room temperature. 9. The method of claim 1, wherein the boronic acid substituted aryls are phenylboronic acids that can be optionally substituted at the para position. 10. The method of claim 9, wherein the boronic acid substituted aryls comprise the general structure of: wherein, R is selected from the group consisting of H, nitro, cyano, Cl, t-Bu, and N(CH3)2. 11. The method of claim 1, wherein the boronic acid substituted aryls is boronic acid substituted naphthalene that may or may not be further substituted. 12. The method of claim 11, wherein the boronic acid substituted naphthalene is 1-naphthylboronic acid. 13. The method of claim 1, wherein the MOF or MOP comprises one or more linking moieties comprising: wherein, R1-R15 are independently selected from the group consisting of H, NH2, CN, OH, SH, P, Br, Cl, I, F, andX is either 1, 2, or 3. 14. The method of claim 13, wherein the MOF or MOP comprises one or more linking moieties comprising: wherein, R1-R3 are independently selected from the group consisting of H, NH2, CN, OH, SH, P, Br, Cl, I, F, and X is either 1, 2, or 3. 15. The method of claim 14, wherein the MOF or MOP comprises one or more linking moieties comprising: 16. The method of claim 1, wherein the MOF or MOP contains a transition metal. 17. The method of claim 16, wherein the MOF or MOP contains Cu. 18. A method to connect aryls by homocoupling comprising contacting a metal organic framework (MOF) with boronic acid substituted aryls, wherein the MOF catalyzes the synthesis of a biaryl through a homo-coupling reaction, and wherein the MOF comprises Cu3(BTC)2 (where BTC is benzene-1,3,5-tricarboxylate). 19. The method of claim 1, wherein the method can be repeated for one or more cycles with the same MOF or MOP.
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