Shang, Yong; Wu, Chenggui; Gao, Qianwen; Liu, Chang; Li, Lisha; Zhang, Xinping; Cheng, Hong-Gang; Liu, Shanshan; Zhou, Qianghui published their research in Nature Communications in 2021. The article was titled 《Diversity-oriented functionalization of 2-pyridones and uracils》.Synthetic Route of C12H17BO2 The article contains the following contents:
A palladium/norbornene cooperative catalysis enabled dual-functionalization of iodinated 2-pyridones I (R = H, Me, Bn, mesityl, MOM, PMB; R1 = CH3, F, Cl, CH2OCH3, CH2C(O)2CH3, 4-ethoxy-4-oxobutyl) and uracils like 6-iodo-1,3-bis(phenylmethyl)-2,4(1H,3H)-pyrimidinedione and 5-iodo-1,3-bis(phenylmethyl)-2,4(1H,3H)-pyrimidinedione. The success of this research depends on the use of two unique norbornene derivatives as the mediator. Readily available alkyl halides R2X (R2 = Me, 4-ethoxy-4-oxobutyl, Bn, etc.; X = Br, I)/tosylate like Me tosylate and aryl bromides R2Br are utilized as ortho-alkylating and -arylating reagents, resp. Widely accessible ipso-terminating reagents, including H/DCO2Na, boronic acid like methylboronic acid/ester like pinacol phenylboronate, terminal alkene R3CH=CH2 (R3 = CH3, CH=CHC6H5, CH=CH2, etc.) and alkyne like triisopropylsilylethyne are compatible with this protocol. Thus, a large number of valuable 2-pyridone derivatives, II including deuterium/CD3-labeled 2-pyridones, bicyclic 2-pyridones, 2-pyridone-fenofibrate conjugate, axially chiral 2-pyridone (97% ee), as well as uracil and thymines III and 1,3-dibenzyl-6-methyl-5-((triisopropylsilyl)ethynyl)pyrimidine-2,4(1H,3H)-dione can be quickly prepared in a predictable manner (79 examples reported), which will be very useful in new drug discovery. In the experimental materials used by the author, we found 4,4,5,5-Tetramethyl-2-phenyl-1,3,2-dioxaborolane(cas: 24388-23-6Synthetic Route of C12H17BO2)
4,4,5,5-Tetramethyl-2-phenyl-1,3,2-dioxaborolane(cas: 24388-23-6) can be used as a substrate in the study of Suzuki–Miyaura coupling of various aryl iodides over SiliaCat Pd(0).Synthetic Route of C12H17BO2
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts