Preparation of 3,4,5-Trisubstituted Oxazolones by Pd-Catalyzed Coupling of N-Alkynyltert-Butyloxycarbamates with Aryl Halides and Related Electrophiles
Zenghui Lu; Weijian Cui; Siyuan Xia; Yihui Bai; Fang Luo; Gangguo Zhu; Journal of Organic Chemistry 77 (2012) 9871–9877; doi:10.1021/jo301794w

data_4027674
_publ_section_title
;
 Preparation of 3,4,5-Trisubstituted Oxazolones by Pd-Catalyzed Coupling
 of N-Alkynyltert-Butyloxycarbamates with Aryl Halides and Related
 Electrophiles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9871
_journal_page_last               9877
_journal_paper_doi               10.1021/jo301794w
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C26 H22 N O3'
_chemical_formula_weight         396.45
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.773(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.874(3)
_cell_length_b                   14.556(2)
_cell_length_c                   12.4930(12)
_cell_measurement_reflns_used    177
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.74
_cell_measurement_theta_min      1.66
_cell_volume                     4145.2(9)
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens XPREP'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_structure_solution    'Siemens SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_sigmaI/netI    0.0670
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16761
_diffrn_reflns_theta_full        27.74
_diffrn_reflns_theta_max         27.74
_diffrn_reflns_theta_min         1.66
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  .0000
_exptl_absorpt_correction_T_min  .0000
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       block
_exptl_crystal_F_000             1672
_exptl_crystal_size_max          .300
_exptl_crystal_size_mid          .200
_exptl_crystal_size_min          .100
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0010(5)
_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   0.870
_refine_ls_hydrogen_treatment    contrs
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4747
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.870
_refine_ls_R_factor_all          0.1317
_refine_ls_R_factor_gt           0.0583
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1411P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1641
_refine_ls_wR_factor_ref         0.2205
_reflns_number_gt                2264
_reflns_number_total             4747
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301794w_si_002.cif
_cod_data_source_block           g
_cod_original_cell_volume        4145.3(9)
_cod_database_code               4027674