Tsuji–Trost Reaction of Non‐Derivatized Allylic Alcohols

Name: Work Video:
Duration: 3 min 30 s
Sunisa Akkarasamiyo; Supaporn Sawadjoon; Andreas Orthaber; Joseph S. M. Samec
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214], 'O‐centered': [18], 'nucleophiles': [19], 'using': [20], 'bidentate': [22], 'BiPhePhos': [23], 'ligand': [24], 'is': [25, 234], 'described.': [26], 'A': [27, 216], 'remarkable': [28], 'effect': [29], 'the': [31, 36, 71, 90, 96, 114, 119, 126, 155, 228, 231, 237], 'counter': [32, 124], 'ion': [33, 125], '(X)': [34], 'XPd[κ': [37], '2': [38, 50, 130], '‐BiPhePhos][η': [39, 51, 131], '3': [40, 42, 52, 54, 103, 105, 132, 134], '‐C': [41, 53, 104, 133], 'H': [43, 55, 106, 135], '5': [44, 56, 107, 136], ']': [45, 57, 108, 137], 'was': [46, 61, 93, 116, 144, 160, 202], 'observed.': [47], 'When': [48, 113], 'ClPd[κ': [49, 100], '(complex': [58, 110, 141], 'I': [59], ')': [60, 143], 'used': [62], 'as': [63, 197, 223], 'catalyst,': [64], 'non‐reproducible': [65], 'results': [66], 'were': [67, 173], 'obtained.': [68], 'Study': [69], 'complex': [72], 'by': [73], 'X‐ray': [74], 'crystallography,': [75], '31': [76], 'P': [77], 'NMR': [78], 'spectroscopy,': [79], 'ESI‐MS': [81], 'showed': [82], 'that': [83], 'decomposition': [85], 'occurred': [86], 'where': [87], 'one': [88], 'phosphite': [91], 'ligands': [92], 'oxidized': [94], 'to': [95, 118, 177, 204], 'corresponding': [97], 'phosphate,': [98], 'generating': [99], '1': [101], '‐BiPhePhosphite‐phosphate][η': [102], 'species': [109], 'II': [111], ').': [112], 'chloride': [115], 'exchanged': [117], 'weaker': [120], 'coordinating': [121], 'OTf': [122], '−': [123, 140], 'more': [127], 'stable': [128], 'Pd[κ': [129], '+': [138], '+[OTf]': [139], 'III': [142, 147, 159], 'formed.': [145], 'Complex': [146, 158], 'performed': [148], 'better': [149], 'gave': [151], 'higher': [152], 'enantiospecificities': [153, 183], 'in': [154, 162, 175, 207, 227, 236], 'reactions.': [157], 'evaluated': [161], 'Tsuji–Trost': [163], 'reactions': [164, 192], 'stereogenic': [166], 'alcohols.': [169], 'The': [170, 200], 'desired': [171], 'products': [172], 'obtained': [174], 'good': [176], 'excellent': [178], 'yields': [179], '(71–98': [180], '%)': [181, 185], '(73–99': [184], 'for': [186], 'both': [187], 'inter‐': [188], 'intramolecular': [190], 'only': [194], 'water': [195], 'generated': [196], 'by‐product.': [199], 'methodology': [201], 'applied': [203], 'key': [205, 225], 'steps': [206], 'total': [208], 'synthesis': [209], '(': [211], 'S': [212], ')‐cuspareine': [213], '(+)‐lentiginosine.': [215], 'reaction': [217], 'mechanism': [218], 'involving': [219], 'palladium': [221], 'hydride': [222], 'intermediate': [226], 'activation': [229], 'hydroxyl': [232], 'group': [233], 'proposed': [235], 'overall': [238], 'transformation.': [239]}, 'cited_by_api_url': 'https://api.openalex.org/works?filter=cites:W2768596599', 'counts_by_year': [{'year': 2024, 'cited_by_count': 3}, {'year': 2023, 'cited_by_count': 5}, {'year': 2022, 'cited_by_count': 8}, {'year': 2021, 'cited_by_count': 3}, {'year': 2020, 'cited_by_count': 6}, {'year': 2019, 'cited_by_count': 8}, {'year': 2018, 'cited_by_count': 6}], 'updated_date': '2024-12-24T19:24:44.408418', 'created_date': '2017-12-04'}
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