81462-07-9Relevant articles and documents
Electrophotochemical Ring-Opening Bromination oftert-Cycloalkanols
Yamamoto, Kosuke,Toguchi, Hiroyuki,Kuriyama, Masami,Watanabe, Shin,Iwasaki, Fumiaki,Onomura, Osamu
, p. 16177 - 16186 (2021/09/13)
An electrophotochemical ring-opening bromination of unstrainedtert-cycloalkanols has been developed. This electrophotochemical method enables the oxidative transformation of cycloalkanols with 5- to 7-membered rings into synthetically useful ω-bromoketones without the use of chemical oxidants or transition-metal catalysts. Alkoxy radical species would be key intermediates in the present transformation, which generate through homolysis of the O-Br bond in hypobromite intermediates under visible light irradiation.
Oxidative C–H alkynylation of 3,6-dihydro-2H-pyrans
Zhao, Ran,Feng, Guidong,Xin, Xiaodong,Guan, Honghao,Hua, Jing,Wan, Renzhong,Li, Wei,Liu, Lei
supporting information, p. 1432 - 1434 (2019/03/28)
Current synthesis of α-substituted 3,6-dihydro-2H-pyrans dominantly relies on functional group transformation. Herein, a direct and practical oxidative C–H alkynylation and alkenylation of 3,6-dihydro-2H-pyran skeletons with a range of potassium trifluoro
Lithium-Catalyzed Thiol Alkylation with Tertiary and Secondary Alcohols: Synthesis of 3-Sulfanyl-Oxetanes as Bioisosteres
Croft, Rosemary A.,Mousseau, James J.,Choi, Chulho,Bull, James A.
supporting information, p. 818 - 821 (2017/12/26)
3-Sulfanyl-oxetanes are presented as promising novel bioisosteric replacements for thioesters or benzyl sulfides. From oxetan-3-ols, a mild and inexpensive Li catalyst enables chemoselective C?OH activation and thiol alkylation. Oxetane sulfides are formed from various thiols providing novel motifs in new chemical space and specifically as bioisosteres for thioesters due to their similar shape and electronic properties. Under the same conditions, various π-activated secondary and tertiary alcohols are also successful. Derivatization of the oxetane sulfide linker provides further novel oxetane classes and building blocks. Comparisons of key physicochemical properties of the oxetane compounds to selected carbonyl and methylene analogues indicate that these motifs are suitable for incorporation into drug discovery efforts.