Rhodium-catalyzed C-H functionalization-based approach to eight-membered lactams.
نویسندگان
چکیده
A Rh(iii) catalyzed formal [4 + 2 + 2] cyclization of N-pivaloyloxybenzamides 1 with 1,6-allene-enes 2 by C-H functionalization is reported. The reactions occur at room temperature and are compatible with air and moisture with a tolerance of many synthetically useful functional groups. The follow-up modifications of the products have been demonstrated. After careful mechanistic studies and DFT calculation, a reaction mechanism was proposed.
منابع مشابه
Rhodium-catalyzed C–H functionalization-based approach to eight-membered lactams† †Electronic supplementary information (ESI) available: Data for new compounds and experimental procedures and theoretical studies on mechanisms. CCDC 979559 and 990983. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5sc00092k Click here for additional data file. Click here for additional data file.
Laboratory of Molecular Recognition an Zhejiang University, Hangzhou 310027, Zh ac.cn State Key Laboratory of Organometallic C Chemistry, Chinese Academy of Sciences, [email protected] Shanghai Key Laboratory of Magnetic Reson Normal University, Shanghai 200062, P. R. † Electronic supplementary information ( and experimental procedures and theor 979559 and 990983. For ESI and crystallo format s...
متن کاملEnantioselective Synthesis of Spiroindenes by Enol-Directed Rhodium(III)-Catalyzed C–H Functionalization and Spiroannulation
Chiral cyclopentadienyl rhodium complexes promote highly enantioselective enol-directed C(sp(2))-H functionalization and oxidative annulation with alkynes to give spiroindenes containing all-carbon quaternary stereocenters. High selectivity between two possible directing groups, as well as control of the direction of rotation in the isomerization of an O-bound rhodium enolate into the C-bound i...
متن کاملA Highly Selective Amidation of Azoxybenzenes with Sulfonamides via Rhodium(III)-Catalyzed C–H Activation
A new amidation of azoxybenzenes with sulfonamides catalyzed by a rhodium(III) salt has been developed. This sulfonamidation proceeds efficiently under mild reaction conditions to generate new C– N bonds through C–H bond activation and functionalization, affording the corresponding 2-sulfonamidoazoxybenzenes in good yields with high regioselectivity.
متن کاملEnantioselective Intermolecular C-H Functionalization of Allylic and Benzylic sp(3) C-H Bonds Using N-Sulfonyl-1,2,3-triazoles.
The enantioselective intermolecular sp(3) C-H functionalization at the allylic and benzylic positions was achieved using rhodium-catalyzed reactions with 4-phenyl-N-(methanesulfonyl)-1,2,3-triazole. The optimum dirhodium tetracarboxylate catalyst for these reactions was Rh2(S-NTTL)4. The rhodium-bound α-imino carbene intermediates preferentially reacted with tertiary over primary C-H bonds in g...
متن کاملAll-Carbon [3+3] Oxidative Annulations of 1,3-Enynes by Rhodium(III)-Catalyzed C–H Functionalization and 1,4-Migration**
1,3-Enynes containing allylic hydrogens cis to the alkyne function as three-carbon components in rhodium(III)-catalyzed, all-carbon [3+3] oxidative annulations to produce spirodialins. The proposed mechanism of these reactions involves the alkenyl-to-allyl 1,4-rhodium(III) migration.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Chemical science
دوره 6 4 شماره
صفحات -
تاریخ انتشار 2015