80716-34-3Relevant academic research and scientific papers
Semicarbazide: A Transient Directing Group for C(sp3)?H Arylation of 2-Methylbenzaldehydes
Wen, Fei,Li, Zheng
supporting information, p. 133 - 138 (2019/11/28)
Semicarbazide as an effective transient directing group for C(sp3)?H arylation of 2-methylbenzaldehydes is described. Various substituted 2-benzylbenzaldehydes are efficiently synthesized by this strategy. The salient features of this protocol are the use of inexpensive transient directing group, wide scope of substrates with good functional group compatibility, up to 98% yield, and applicability to gram scale. (Figure presented.).
Glycinamide hydrochloride as a transient directing group: Synthesis of 2-benzylbenzaldehydes by C(sp3)?H arylation
Wen, Fei,Li, Zheng
supporting information, p. 3462 - 3474 (2020/08/10)
Glycinamide hydrochloride as an inexpensive and commercially available transient directing group for the C(sp3)?H arylation of 2-methylbenzaldehydes is described. A series of practical 2-benzylbenzaldehydes bearing various functional groups are efficiently synthesized in satisfactory yield by this strategy. This method can also be extended to gram scale.
Organic chemistry: Functionalization of C(sp3)-H bonds using a transient directing group
Zhang, Fang-Lin,Hong, Kai,Li, Tuan-Jie,Park, Hojoon,Yu, Jin-Quan
, p. 252 - 256 (2016/01/25)
Proximity-driven metalation has been extensively exploited to achieve reactivity and selectivity in carbon-hydrogen (C-H) bond activation. Despite the substantial improvement in developing more efficient and practical directing groups, their stoichiometric installation and removal limit efficiency and, often, applicability as well. Here we report the development of an amino acid reagent that reversibly reacts with aldehydes and ketones in situ via imine formation to serve as a transient directing group for activation of inert C-H bonds. Arylation of a wide range of aldehydes and ketones at the β or γ positions proceeds in the presence of a palladium catalyst and a catalytic amount of amino acid. The feasibility of achieving enantioselective C-H activation reactions using a chiral amino acid as the transient directing group is also demonstrated.
REARRANGEMENT AND FRAGMENTATION REACTIONS OF BLOCKED AROMATIC ALCOHOLS.
Bhattacharya,Miller
, p. 3242 - 3247 (2007/10/02)
A report is presented on the products obtained from reaction of alcohol and its secondary analogue with acidic solutions. It is found that in solutions containing acetic anhydride both give solely products resulting from molecular rearrangements. Factors responsible for determining the reaction products and reactivities of the starting alcohols are discussed.
