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_4027675
_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            'C24 H17 N O2'
_chemical_formula_weight         351.39
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 97.093(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9736(2)
_cell_length_b                   17.1873(6)
_cell_length_c                   15.2945(5)
_cell_measurement_reflns_used    6497
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      1.79
_cell_volume                     1819.13(10)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28522
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         1.79
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  .990
_exptl_absorpt_correction_T_min  .969
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          .52
_exptl_crystal_size_mid          .32
_exptl_crystal_size_min          .12
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0095(12)
_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   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0496P)^2^+0.1916P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1148
_reflns_number_gt                2779
_reflns_number_total             4165
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301794w_si_003.cif
_cod_data_source_block           a
_cod_database_code               4027675