Palladium-Catalyzed Intramolecular C-Arylation of Benzylic Carbon: Synthesis of 3-Benzoxazolylisoindolinones by a Sequence of Ugi-4CR/Postfunctionalization
Angela Salcedo; Luc Neuville; Jieping Zhu; Journal of Organic Chemistry 73 (2008) 3600–3603; doi:10.1021/jo800266y

data_4023398
_publ_contact_author_address
;ICSN-CNRS
1 avenue de la Terrasse
91198 Gif sur Yvette
France

;
_publ_contact_author_email       zhu@icsn.cnrs-gif.fr
_publ_contact_author_fax         '33 (1) 69077247'
_publ_contact_author_name        'Jieping ZHU'
_publ_contact_author_phone       '33 (1) 69823131'
_publ_section_title
;
 Palladium-Catalyzed Intramolecular C-Arylation of Benzylic Carbon:
 Synthesis of 3-Benzoxazolylisoindolinones by a Sequence of
 Ugi-4CR/Postfunctionalization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3600
_journal_page_last               3603
_journal_paper_doi               10.1021/jo800266y
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C18 H16 N2 O3'
_chemical_formula_sum            'C18 H16 N2 O3'
_chemical_formula_weight         308.33
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             29-10-07
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.886(1)
_cell_length_b                   11.995(1)
_cell_length_c                   23.999(2)
_cell_measurement_reflns_used    7129
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.26
_cell_measurement_theta_min      0.41
_cell_volume                     3133.7(5)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) COLLECT (Hooft, 1998)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997) COLLECT (Hooft, 1998)'
_computing_data_reduction        'HKL package (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1980-2004)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .994
_diffrn_measured_fraction_theta_max .994
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8064
_diffrn_reflns_theta_full        21.26
_diffrn_reflns_theta_max         21.26
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bipyramid
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         .120
_refine_diff_density_min         -.118
_refine_diff_density_rms         .030
_refine_ls_extinction_coef       0.0066(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         2001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0479P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0986
_reflns_number_gt                1523
_reflns_number_total             2001
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800266y-File001_2.cif
_cod_data_source_block           angelasalcedo081
_cod_database_code               4023398