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Catalytic Intermolecular Carboamination of Unactivated Alkenes Via Directed Aminopalladation Zhen Liu,† Yanyan Wang,‡ Zichen Wang,† Tian Zeng,† Peng Liu,*,‡ Keary M

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Catalytic Intermolecular Carboamination of Unactivated Alkenes Via Directed Aminopalladation Zhen Liu,† Yanyan Wang,‡ Zichen Wang,† Tian Zeng,† Peng Liu,*,‡ Keary M Catalytic Intermolecular Carboamination of Unactivated Alkenes via Directed Aminopalladation Zhen Liu,† Yanyan Wang,‡ Zichen Wang,† Tian Zeng,† Peng Liu,*,‡ Keary M. Engle*,† †Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States ‡Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States Supporting Information Placeholder ABSTRACT: An intermolecular 1,2-carboamination of unactivated substrates, wherein a removable bidentate directing group enables alkenes proceeding via a Pd(II)/Pd(IV) catalytic cycle has been regioselective aminopalladation and facilitates subsequent oxidative developed. To realize this transformation, a cleavable bidentate addition and reductive elimination. This method enables directing group is used to control the regioselectivity of straightforward access to drug molecules and natural products bearing aminopalladation and stabilize the resulting organopalladium(II) γ-amino acid and γ-lactam structural motifs and is amenable to intermediate, such that oxidative addition to a carbon electrophile combinatorial synthesis (Scheme 1D). outcompetes potential β-hydride elimination. Under the optimized reaction conditions, a broad range of nitrogen nucleophiles and carbon Scheme 1. Background and Project Synopsis electrophiles were compatible coupling partners in this reaction, A. Intramolecular carboamination of alkenes (Wolfe, 2004) affording moderate to high yields. The products of this reaction can be cat. Pd2(dba)3 NR easily converted to free γ-amino acids and γ-lactams, both of which are NHR cat. ligand common structural motifs found in drug molecules and bioactive + Ar–Br Ar compounds. DFT calculations shed light on the reactivity trends of different carbon electrophiles. B. Two-component intermolecular syn-carboamination (Rovis, 2015) NPhth t-Bu O CO2R O cat. Cp* Rh(III) RO2C + CO2R INTRODUCTION CO2R MeOH Ar Ar NPhth Nitrogen-containing small molecules possess diverse bioactivity and are commonly encountered as pharmaceutical agents, C. Three-component intermolecular anti-carboamination (this work) 1 agrochemicals, and natural products. 1,2-Carboamination of alkenes R1 R2 cat. Pd(OAc)2 offers a potentially powerful platform for accessing structurally O N KHCO3 (1 equiv) [C] O H R + R complex amines from comparatively common and inexpensive starting AQ AQ [C]–X HFIP, 100 ºC materials. However, despite extensive effort over the past decades, N R1 R2 realizing a catalytic intermolecular carboamination of unactivated [C] = aryl, vinyl, alkyl, alkynyl alkenes has remained a challenge. During the last decade, Wolfe and D. Potential natural products or drug targets Me others have developed a series of palladium(0)-catalyzed R Me intramolecular carboamination methods by using alkene substrates 2 Me O O with a tethered nitrogen nucleophile (Scheme 1A). These O H N N transformations are an effective means of accessing various 2 OH H2N H2N O azaheterocycles. A significant advance was reported in 2015 by Piou OH Me and Rovis using rhodium(III) as a catalyst to promote coupling of an Baclofen (R = Cl) Lyrica Brivaracetam Phenibut (R = H) enoxyphthalimide (which serves as both the nitrogen and carbon O 3 NMe source) with an electronically activated alkene. (Scheme 1B). Ph N Three-component intramolecular carboamination reactions that O OH proceed with unactivated alkenes would be highly enabling but remain N 4 MeN underdeveloped. O HN H N O Based on our previous success in palladium(II)-catalyzed alkene 2 O O hydrofunctionalization5,6 and 1,2-dicarbofunctionalization,7 we Rolipram Phenylpiracetam Cynometrine questioned whether a chelation-stabilized aminopalladated Wacker-type intermediate could be intercepted with a carbon electrophile as a strategy for alkene carboamination.8,9 By strategic use RESULTS AND DISCUSSION of a proximal removable directing group to control the regioselectivity of aminopalladation and stabilize the resulting alkylpalladium(II) To initiate our study, 3-butenoic acid masked as the corresponding 9a,b,f intermediate, we envisioned that we could develop a highly selective 8-aminoquinoline (AQ) amide (1a) was selected as the pilot alkene and heretofore elusive three-component carboamination reaction via a substrate, and phthalimide (2a) and 4-iodoanisole (3q) were Pd(II)/Pd(IV) catalytic cycle (Scheme 1C). To the best of our investigated as potential coupling partners. During initial screening, we knowledge, palladium(II)-catalyzed intermolecular three-component were delighted to find that 23% of the desired product was formed by carboamination of unactivated alkenes is unprecedented.10 Herein, we using 10 mol% Pd(OAc)2 as the catalyst and 1 equiv K2CO3 as the base describe a new catalytic carboamination method for unactivated alkene in toluene as solvent (Table 1, entry 1). Different inorganic bases were tested (entries 1–3), and K2HPO4 gave the highest yield (up to 34%) in exception, and we were able to obtain carboaminated product 4l in toluene. We then discovered that when hexafluoroisopropanol (HFIP) 70% yield. Surprisingly, the presence of a free hydroxyl group was well was used as solvent, the yield increased to 44% (entry 6). Further tolerated (4m), as were the ether and ester groups in the optimization revealed that lowering temperature to 100 °C and steroid-derived alkenyl iodide (4n). With E-alkenyl iodides, the switching the inorganic base to KHCO3 gave a higher yield of 54% reaction was completely stereoretentive in terms of alkene geometry, (entry 8). Finally, we found that by increasing the amount of the whereas with Z-alkenyl iodides, there was noticeable erosion of the 4-iodoanisole (3q) to 6 equiv, the 1,2-aminoarylated product 4q was Z-stereochemistry in the product compared to the starting material generated in 61% yield (entry 10). Gratifyingly, when we tested the (4d–4g and 4j).11 Aryl iodides were also competent electrophiles, and more reactive electrophile styrenyl iodide (3a, 4 equiv), the substituents on the para or meta position were tolerated under the corresponding aminovinylated product 4a was isolated in 85% yield optimized conditions, with electron-withdrawing groups attenuating under the optimized reaction conditions (entry 11). reactivity (4o–4s). Heteroaryl iodides, bearing a thienyl group (3t and 3u), are excellent coupling partners in this reaction. While a pyridine-based aryl iodides are not very reactive under the standard Table 1. Optimization of the Reaction Conditions condition, requiring a substituent at 2-position to diminish the pyridine nitrogen coordination (4v). In general, aryl iodides were less reactive N R O in this transformation, requiring additional equivalents to achieve H Ph O O N O I Pd(OAc)2 N moderate yields. Additionally, we managed to install an alkynyl group + + 3a H N N H O O by using (bromoethynyl)triisopropylsilane (3w) as the electrophile in N or Base good yield (4w). In general, alkenyl iodides and (4-OMe)C4H4I 1a 2a 3q 4a or 4q (bromoethynyl)triisopropylsilane were the most reactive electrophiles, followed by electron-rich aryl iodides, and finally electron-poor aryl entry Electrophile Solvent Base Temp. (ºC) Yieldb (%) iodides (vide infra), similar to the trend that was observed in our 7 previously published 1,2-dicarbofunctionalization. 1 3q K CO 110 (23) toluene 2 3 Table 2. Carbon Electrophile Scopea 2 3q toluene Cs2CO3 110 trace H O O N O 10 mol% Pd(OAc)2 3 3q toluene K HPO 110 (34) 1 equiv KHCO O 2 4 3 R O N + + R I H HFIP, 100 ºC N N AQ 4 3q MeCN K HPO 110 trace (AQ) 2 4 O 1a 2a 3a–w 4a–w 5 3q DCE K2HPO4 110 (7) X 6 3q HFIP K2HPO4 110 (44) O O 7 3q HFIP KHCO3 110 38 O MeO AQ F3C AQ O N N AQ O O O O 8 3q HFIP 100 54 AQ KHCO3 O N O O N O 9 3q HFIP K2HPO4 100 (15) c 4a, 85% 4b (X = Cl), 81% b b 10 3q HFIP KHCO3 100 61 4d, 82% 4e, 43% 4c (X = Br), 65% Z/E = 2.9:1 Z/E = 8.4:1 11 3a HFIP KHCO 100 85 Me 3 Ph a Reaction conditions: 1a (0.1 mmol), 2a (1.5 equiv), 3a or 3q (4 O S AQ O O equiv), Pd(OAc)2 (10 mol %), base (1 equiv), HFIP (0.2 mL), air, N O 10–24 h. bIsolated yield. Values in parentheses represent yields O O AQ AQ N N AQ 1 O O O O determined by H NMR analysis of the crude reaction mixture using O N O c CH2Br2 as internal standard. 6 equiv of aryl iodide 3q. c 4f, 84%b 4g, 79% 4h, 76% 4i, 97% Z/E = 2:1 Z/E = 1:4 Having optimized the reaction conditions, we next investigated the Me Me substrate scope of this palladium(II)-catalyzed alkene carboamination O Me O O reaction. First, various carbon electrophiles were tested with alkene AQ AQ AQ N N substrate 1a and phthalimide (2a) as the nitrogen nucleophile (Table O O O O O N O 2). An array of E- and Z-styrenyl iodides containing different substituents on the aromatic ring were found to be reactive, providing ! 4j, 71%b 4k, 60% [X-ray] 4l, 70% the corresponding carboaminated products in moderate to high yields Z/E = 1.9:1 (4a–4e). Notably, bromide and chloride groups were tolerated, OH O O presenting the opportunity for subsequent diversification via Me O AQ O O MeO Me AQ cross-coupling. A 2-thienyl group was well tolerated on the alkenyl AQ O Me H N iodide (4f), and a 1-iodo-1,3-diene was similarly competent as a O N O N O O H H O reaction partner (4g). Several alkyl-substituted alkenyl iodides were MeO OMe H also suitable electrophiles in this transformation (4h–4n), including a 4m, 78% 4n, 84%d 4o, 53%e 2,2-dimethyl-substituted example (4k). In general, alkenyl iodides d.r.
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