Palladium-Catalyzed Coupling of Haloalkynes with Allyl Acetate: A Regio- and Stereoselective Synthesis of (Z)-β-Haloenol Acetates
Xiaoyi Chen; Dongxu Chen; Zenghui Lu; Lichun Kong; Gangguo Zhu; Journal of Organic Chemistry 76 (2011) 6338–6343; doi:10.1021/jo2005318

data_4026474
_publ_section_title
;
 Palladium-Catalyzed Coupling of Haloalkynes with Allyl Acetate: A Regio-
 and Stereoselective Synthesis of (Z)-\b-Haloenol Acetates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6338
_journal_page_last               6343
_journal_paper_doi               10.1021/jo2005318
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C15 H17 Cl O4'
_chemical_formula_sum            'C15 H17 Cl O4'
_chemical_formula_weight         296.74
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                74.345(7)
_cell_angle_beta                 84.975(6)
_cell_angle_gamma                83.654(6)
_cell_formula_units_Z            4
_cell_length_a                   8.9785(9)
_cell_length_b                   11.6414(12)
_cell_length_c                   14.8917(17)
_cell_measurement_reflns_used    4499
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      1.42
_cell_volume                     1486.9(3)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEXII (Bruker, 2006)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II area-detector diffractometer'
_diffrn_measurement_method       'phi and omega 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  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23798
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         6784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0714P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1373
_reflns_number_gt                4229
_reflns_number_total             6784
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2005318_si_002.cif
_cod_data_source_block           a
_cod_database_code               4026474