<p>The 25th ISHC Congress–Santa Barbara CA Aug 23-28, 2015</p><p>! Important notes:</p><p>You MUST use this template. If you don’t use it your abstract WILL be rejected.</p><p>Do NOT enter author and institution information on this form. You will be able to enter this information online when you submit the abstract.</p><p>Do NOT write outside the boxes. Any text or images outside the boxes will be deleted.</p><p>Do NOT alter this form by deleting parts of it or adding new boxes. Simply enter your information into the boxes. The form will be automatically processed – if you alter it your submission will not be processed correctly.</p><p>An un-sized >10point font is highly recommended for Chemdraw graphics</p><p>Save this file in .doc or .docx format. </p><p>Title: Palladium-Catalyzed Amidation by Chemoselective C(sp3)-H functionalization: Concise Route to Oxindoles and its application</p><p>Abstract: (Your abstract must use Normal style and must fit into the box. Do not enter author details) The oxindole moiety is a core structure in many complex natural products; such natural products often possess interesting biological activities. This structure has also drawn the attention of medicinal chemists because of its potential as an important pharmacophore. In the course of the synthetic studies of spirooxindole skeleton, we focused on the utilities of carbamoyl chloride, which undergo oxidative addition to palladium catalyst. If C(sp 3)-H bond activation is occurred after the oxidative addition, oxindoles would be accessed concisely. When we started the project, several groups reported the related cyclization using palladium catalyst via C(sp3)-H bond activation of a methyl group and the following reductive elimination. Thus we examined the formation of oxindoles from carbamoyl chloride bearing an alkyl group in proper position.</p><p>3 mol% Pd(OAc)2 2 2 R2 R 6 mol% Ad2PBu R R2 Cs2CO3 (1.1 eq.) O PivNHOH (0.3 eq.) O (1) N N Cl CO (1 atm) 1 Me R1 Me mesitylene, 120 °C R 88% (R1 = Me, R2 = H)</p><p>The cyclization of carbamoyl chloride (R1 = Me, R2 = H), which was prepared 2,6- dimethylaniline, proceeded smoothly under the conditions of palladium acetate (3 mol%), di(1-adamantyl)- n-butylphosphine (6 mol%), Cs2CO3 and N-hydroxypivalamide in mesitylene at 120 °C to give oxindole in 88% yield (eq. 1). These conditions could be applied to several substrates having chloro, methoxy groups and so on. Further studies to disclose the reaction scope and apply to the synthesis of natural products are currently underway and will be reported. </p>