The crystal structure of the title compound, C15H20N2orDippIm, is reported. At 106 (2) K, the molecule has monoclinic
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Purinyl N -directed aroylation of 6-arylpurine ribo- and 2′-deoxyribonucleosides, and mechanistic insights
The purinyl nitrogen atom is an effective metalation director, which in the presence of Pd(OAc)2,t -BuOOH, and aryl aldehydes, leads to acylation of the aryl ring at the C6 position of the purine.
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- Award ID(s):
- 1953574
- PAR ID:
- 10538650
- Publisher / Repository:
- The Royal Society of Chemistry (UK)
- Date Published:
- Journal Name:
- Organic & Biomolecular Chemistry
- Volume:
- 22
- Issue:
- 33
- ISSN:
- 1477-0520
- Page Range / eLocation ID:
- 6718 to 6726
- Subject(s) / Keyword(s):
- Palladium, nucleoside, aldehyde, aroyl, C-H bond activation, radical
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
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P 21/c symmetry with four molecules in the unit cell. The imidazole ring is rotated 80.7 (1)° relative to the phenyl ring. Intermolecular stabilization primarily results from close contacts between the N atom at the 3-position on the imidazole ring and the C—H bond at the 4-position on the neighboringDippIm, with aryl–aryl distances outside of the accepted distance of 5 Å for π-stacking. -
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Abstract The synthesis of tris(
ortho ‐carboranyl)borane (Bo Cb3), a single site neutral Lewis superacid, in one pot from commercially available materials is achieved. The high fluoride ion affinity (FIA) confirms its classification as a Lewis superacid and the Gutmann‐Beckett method as well as adducts with Lewis bases indicate stronger Lewis acidity over the widely used fluorinated aryl boranes. The electron withdrawing effect ofortho ‐carborane and lack of pi‐delocalization of the LUMO rationalize the unusually high Lewis acidity. Catalytic studies indicate that Bo Cb3is a superior catalyst for promoting C−F bond functionalization reactions than tris(pentafluorophenyl)borane [B(C6F5)3]. -
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Abstract The synthesis of tris(
ortho ‐carboranyl)borane (Bo Cb3), a single site neutral Lewis superacid, in one pot from commercially available materials is achieved. The high fluoride ion affinity (FIA) confirms its classification as a Lewis superacid and the Gutmann‐Beckett method as well as adducts with Lewis bases indicate stronger Lewis acidity over the widely used fluorinated aryl boranes. The electron withdrawing effect ofortho ‐carborane and lack of pi‐delocalization of the LUMO rationalize the unusually high Lewis acidity. Catalytic studies indicate that Bo Cb3is a superior catalyst for promoting C−F bond functionalization reactions than tris(pentafluorophenyl)borane [B(C6F5)3]. -
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Abstract A variety of 1‐aryl‐1,3‐dienes were isomerized from
E toZ isomers by photocatalysis using Ru(bpy)3[PF6]2and blue LED light. Enrichment of theZ ‐isomer is thought to occur by selective triplet energy transfer from the photocatalyst to the stereoisomeric mixture. The 1,3‐diene starting materials are easily made by catalytic ene‐yne metathesis (EYM). To access 1,3‐dieneZ ‐stereoisomers directly, a one pot procedure was developed. Additional 1,3‐dienes were investigated for both isomerization andZ ‐enrichment. The combination of cross EYM with photocatalysis allows for the stereoconvergent synthesis ofZ ‐1,3‐dienes. -
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Abstract Computational studies revealed that dirhodium tetrakis(1,2,2‐triarylcyclopropanecarboxylate) (Rh2(TPCP)4) catalysts adopt distinctive high symmetry orientations, which are dependent on the nature of the aryl substitution pattern. The parent catalyst, Rh2(TPCP)4, and those with a
p ‐substituent at the C1 aryl, such as Rh2(p ‐BrTPCP)4and Rh2(p ‐PhTPCP)4, adopt aC 2‐symmetric structure. Rh2(3,5‐di(p ‐t BuC6H4)TPCP)4, 3,5‐disubstituted at the C1 aryl, adopts aD 2‐symmetric structure, whereas catalysts with ano ‐substituent at the C1 aryl, such as Rh2(o ‐Cl‐5‐BrTPCP)4,adopt aC 4‐symmetric structure.
